Deprotection Step Patents (Class 536/25.31)
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Patent number: 11851593Abstract: The present disclosure discloses a nanoparticle, a nanoparticle layer patterning method and related application. When the nanoparticle disclosed by the present disclosure is adopted to form a patterned nanoparticle layer on a substrate, a photosensitive material is added in the nanoparticle, then a protective group in a first ligand is dissociated to form an amino under the irradiation of light with a preset wavelength, a second ligand including an amino is formed on a surface of a nanometer particle, and a polarity of the second ligand is different from a polarity of the first ligand; and the amino of the second ligand is cross-linked with an adjacent nanoparticle.Type: GrantFiled: June 18, 2021Date of Patent: December 26, 2023Assignees: Beijing BOE Technology Development Co., Ltd., BOE Technology Group Co., Ltd.Inventors: Zhuo Chen, Tieshi Wang
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Patent number: 11814450Abstract: Embodiments of the present application relate to porous polymeric beads solid support for use in oligonucleotide synthesis and the method of producing and using the same. Further embodiments relate to porous polymeric beads and method for preparing and using the same.Type: GrantFiled: October 20, 2022Date of Patent: November 14, 2023Assignee: Hongene Biotech CorporationInventors: Jingshe Song, John Michael Cue, Yun-Chiao Yao, David Yu, Aldrich N. K. Lau
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Patent number: 11813338Abstract: The invention relates to compositions and methods for diagnosing as well as treating cancer diseases associated with choline kinase (ChoK). Specifically, the invention relates to a composition comprising an intrinsically fluorescent choline kinase (ChoK) inhibitor or a ChoK inhibitor operably linked to a fluorescent dye. The composition is capable of diagnosing and/or treating cancer diseases associated with ChoK.Type: GrantFiled: March 12, 2014Date of Patent: November 14, 2023Assignee: THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIAInventors: Edward J. Delikatny, Anatoliy V. Popov, Sean P. Arlauckas
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Patent number: 11692006Abstract: This invention is intended to discover a novel solvent that can be used as an alternative to toluene in the step of deprotection in the method of solid-phase nucleic acid synthesis. With the use of such novel solvent, various problems caused by the use of toluene are dissolved. This invention is also intended to provide a method of solid-phase nucleic acid synthesis in which protected nucleoside phosphoramidites in which a protective group is bonded to a hydroxyl group at the 5?position or the 3? position of a nucleoside are sequentially bound on a solid phase carrier, where a reaction of removing the protecting group from the protected nucleoside phosphoramidite is carried out in a solution comprising an acid with a pKa of 0.2 to 0.8 and acetonitrile.Type: GrantFiled: July 4, 2018Date of Patent: July 4, 2023Assignee: Nitto Denko CorporationInventors: Masafumi Iwamoto, Tsuyoshi Mukobata, Akira Yokouchi
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Patent number: 11661436Abstract: Methods for preparing 3?-O-amino-2?-deoxyribonucleoside-5?-triphosphates with reduced 3?-hydroxy-2?-deoxyribonucleoside-5?-triphosphate contamination by converting 3?-(N-acetone-oxime)-2?-deoxynucleoside triphosphate to 3?-O-amine-2?-deoxynucleoside triphosphate by treatment with an aryl-oxyamine and compositions produced therefrom.Type: GrantFiled: March 26, 2021Date of Patent: May 30, 2023Assignee: DNA SCRIPT SASInventors: Filip Wojciechowski, Thomas Ybert
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Patent number: 11623940Abstract: The invention relates to the use of polyphosphate containing species in a method of nucleic acid synthesis, to methods of nucleic acid synthesis, and to the use of kits comprising said polyphosphate containing species. The invention also relates to the use of polyphosphate containing species for the capping of 3?-terminal hydroxyl moieties using terminal transferases.Type: GrantFiled: September 14, 2018Date of Patent: April 11, 2023Assignee: Nuclera Nucleics Ltd.Inventors: Michael Chen, Jiahao Huang, Gordon McInroy
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Patent number: 11427801Abstract: The present disclosure relates to a simple, fast, and low cost method for 3D microvascular imaging, termed “scatter labeled imaging of microvasculature in excised tissue” (SLIME). The method can include perfusing a contrast agent through vasculature of a tissue sample with a contrast perfusing unit (22). The contrast agent can include colloids and a dispersant. After the contrast agent is perfused through the vasculature, the vasculature of the tissue sample can be treated with a cross-linking agent delivery unit (24) providing a molecule that cross links with at least a portion of the dispersant to form a sticky, non-Newtonian polymer that prevents leakage of the contrast agent out of the vasculature of the tissue sample. The tissue sample can then be immersed in a solution comprising a clearing agent with an optical clearing unit (26) and subsequently imaged.Type: GrantFiled: November 9, 2018Date of Patent: August 30, 2022Assignees: CASE WESTERN RESERVE UNIVERSITY, UNIVERSITY HOSPITALS CLEVELAND MEDICAL CENTERInventors: Michael W. Jenkins, Yehe Liu
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Patent number: 9896472Abstract: A method of deprotecting a solid support bound polynucleotide includes the step of contacting the polynucleotide with a composition comprising a diamine under conditions sufficient to deprotect the 2?-protected ribonucleotide residue. The solid support bound polynucleotide has at least one 2?-protected ribonucleotide residue, which has the following structure: wherein BP is a protected or unprotected heterocycle; R12 is a protecting group selected from a hydrocarbyl, a substituted hydrocarbyl, an aryl, and a substituted aryl; X is O or S; and PG is a thionocarbamate protecting group.Type: GrantFiled: September 14, 2015Date of Patent: February 20, 2018Assignee: Agilent Technologies, Inc.Inventors: Douglas J. Dellinger, Joel Myerson, Agnieszka Sierzchala, Geraldine F. Dellinger, Zoltan Timar
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Patent number: 9758546Abstract: Provided herein are methods for the synthesis of oligomeric compounds wherein removal of the 5?-terminal trityl group is performed at reduced temperature and lower pH relative to standard methods. In certain embodiments, the present methods provide detritylated oligomeric compounds having a reduced percentage of depurination relative to the same detritylated oligomeric compounds prepared using standard methods. In certain embodiments, the present methods provide detritylated oligomeric compounds with increased purity relative to the same detritylated oligomeric compounds prepared using standard methods. In certain embodiments, the present method provide an increased rate of detritylation compared to standard methods.Type: GrantFiled: October 21, 2014Date of Patent: September 12, 2017Assignee: Ionis Pharmaceuticals, Inc.Inventor: Dana Chreng
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Patent number: 9657296Abstract: Compounds comprising an oligonucleotide moiety covalently linked to a lipid moiety are disclosed. The oligonucleotide moiety comprises a sequence that is complementary to the RNA component of human telomerase. The compounds inhibit telomerase activity in cells with a high potency and have superior cellular uptake characteristics.Type: GrantFiled: May 18, 2015Date of Patent: May 23, 2017Assignee: Geron CorporationInventors: Sergei Gryaznov, Krisztina Pongracz
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Patent number: 9085797Abstract: The invention relates to a process for deblocking substantially a blocked, detectably labeled oligonucleotide by contacting the blocked detectably labeled oligonucleotide with an effective amount of a nucleophilic amino compound under conditions that result in substantial deblocking of the oligonucleotide, thereby giving the substantially deblocked oligonucleotide.Type: GrantFiled: August 9, 2013Date of Patent: July 21, 2015Assignee: Life Technologies CorporationInventors: Gulilat Gebeyehu, Richard Pires
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Publication number: 20150119564Abstract: Methods for removing 1,3,5-trimethylhexahydro-1,3,5-triazine and N-methylenemethanamine from a N-methylimidazole and methods for making oligonucleotides using N-methylimidazole are provided. In one embodiment, a method for removing 1,3,5-trimethylhexahydro-1,3,5-triazine and N-methylenemethanamine from a feedstock containing N-methylimidazole includes contacting the feedstock with small or medium pore molecular sieves. The small or medium pore molecular sieves adsorb 1,3,5-trimethylhexahydro-1,3,5-triazine and N-methylenemethanamine from the feedstock. The method further includes separating the small or medium pore molecular sieves from the feedstock.Type: ApplicationFiled: August 28, 2014Publication date: April 30, 2015Inventors: Venkatraman Mohan, Sandra M. Lorenz, Gregory Gajda
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Publication number: 20150080565Abstract: The present invention provides a protected nucleotide for elongation, which can be purified efficiently and in a high yield by a liquid-liquid extraction operation, and can achieve an oligonucleotide production method by a phosphoramidite method. It has been found that the above-mentioned problem can be solved by a particular oligonucleotide comprising a protected base and/or particular oligonucleotide protected by a branched chain-containing aromatic group at 3?-position.Type: ApplicationFiled: September 19, 2014Publication date: March 19, 2015Applicant: Ajinomoto Co., Inc.Inventors: Kunihiro HIRAI, Satoshi Katayama, Takayoshi Torii, Ryotaro Nakaya, Daisuke Takahashi
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Patent number: 8981076Abstract: This invention relates to synthesis of novel -N-FMOC protected nucleosides, succinates, phosphoramidites, corresponding solid supports that are suitable for oligo deoxy nucleosides and RNA oligonucleotide synthesis. Our discovery using N-FMOC as nucleoside base protecting group, which is highly base labile protecting group is a novel approach to obtain highest purity oligonucleotides. This approach is designed to lead to very high purity and very clean oligonucleotide, after efficient removal of the protecting groups and to produce high purity therapeutic grade DNA oligonucleotides, RNA oligonucleotides, diagnostic DNA, diagnostic RNA for microarray platform. The deprotection of FMOC protecting groups of the natural deoxy and ribonucleosides occurs under very mild deprotection conditions such as mild bases, secondary and tertiary amines for removal of such groups under such conditions would allows synthesis of various DNA and RNA of highest purity for diagnostics and therapeutic application.Type: GrantFiled: November 30, 2009Date of Patent: March 17, 2015Assignee: ChemGenes CorporationInventors: Suresh C. Srivastava, Naveen P. Srivastava
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Publication number: 20150072345Abstract: Oligonucleotides with a novel sugar-phosphate backbone containing at least one 2?-arabino-fluoronucleoside and an internucleoside 3?-NH—P(—O)(OR)—O-5? linkage, where R is a positively charged counter ion or hydrogen, and methods of synthesizing and using the inventive oligonucleotides are provided. The inventive phosphoramidate 2?-arabino-fluorooligonucleotides have a high RNA binding affinity to complementary nucleic acids and are base and acid stable.Type: ApplicationFiled: September 11, 2014Publication date: March 12, 2015Inventors: Sergei M. Gryaznov, Ronald G. Schultz
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Publication number: 20150045547Abstract: Methods for preparation of 2?,3?-dideoxynucleotides support structures, such as 2?,3?-dideoxyguanosine, 2?,3?-dideoxyadenosine, and 3?-deoxythymidine support structures are disclosed. Various methods of using such structures are also provided, such as their use for automated DNA synthesis and pyrophosphorolysis activated polymerization.Type: ApplicationFiled: February 5, 2014Publication date: February 12, 2015Applicant: LIFE TECHNOLOGIES CORPORATIONInventors: Zhaochun MA, Khairuzzaman Bashar Mullah, Robert Eason
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Publication number: 20140349292Abstract: Oligonucleotides with a novel sugar-phosphate backbone containing at least one internucleoside 3?-NHP(O)(S?)O-5? linkage, and methods of synthesizing and using the inventive oligonucleotides are provided. The inventive thiophosphoramidate oligonucleotides were found to retain the high RNA binding affinity of the parent oligonucleotide N3??P5? phosphoramidates and to exhibit a much higher acid stability.Type: ApplicationFiled: July 9, 2014Publication date: November 27, 2014Inventors: Sergei Gryaznov, Krisztina Pongracz, Tracy Matray
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Patent number: 8846885Abstract: The present invention provides a protected nucleotide for elongation, which can be purified efficiently and in a high yield by a liquid-liquid extraction operation, and can achieve an oligonucleotide production method by a phosphoramidite method. It has been found that the above-mentioned problem can be solved by a particular oligonucleotide comprising a protected base and/or particular oligonucleotide protected by a branched chain-containing aromatic group at 3?-position.Type: GrantFiled: February 15, 2013Date of Patent: September 30, 2014Assignee: Ajinomoto Co., Inc.Inventors: Kunihiro Hirai, Satoshi Katayama, Takayoshi Torii, Ryotaro Nakaya, Daisuke Takahashi
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Publication number: 20140256928Abstract: A protecting group for 1-nitrogen atom of an indole group including a sulfonylethyl carbamate group, wherein the protecting group is represented by the following General Formula (I) and capable of being removed from the 1-nitrogen atom of the indole group in an aprotic solvent: where R represents an alkyl group, a derivative of the alkyl group, a phenyl group or a derivative of the phenyl group.Type: ApplicationFiled: May 9, 2014Publication date: September 11, 2014Applicant: APTA BIOSCIENCES LTD.Inventor: Tsuyoshi FUJIHARA
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Patent number: 8822671Abstract: A 2?-modified ribonucleoside having an alkoxymethyl protective group can be imparted with a high duplex-forming ability by introducing, as a substituent, a halogen atom into the protective group moiety. A modified form of RNA having a halogen-substituted alkoxymethyl protective group exhibits a high duplex-forming ability that is comparable to the duplex-forming ability of a 2?-O-methyl modified nucleic acid.Type: GrantFiled: November 28, 2011Date of Patent: September 2, 2014Assignees: The University of Tokyo, Chiralgen, Ltd.Inventors: Mamoru Shimizu, Takeshi Wada, Kouichiro Arai
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Patent number: 8816062Abstract: The compounds of formula (I) substantially in exo form or salts thereof, wherein: X is a biradical selected from —(CH2)n—*, —(CH2CH2O)nCH2CH2—*, methylcyclohexyl and methylphenyl; n is an integer ranging between 1 and 30; Y is a radical selected from —COOH, a substituted phosphoramidite radical and N-hydroxysuccinimide ester (or other active ester) of carboxylic acid; and * represents the place through which X binds to Y, are useful in a general process for solid-phase preparation of maleimide-oligonucleotide derivatives.Type: GrantFiled: May 2, 2011Date of Patent: August 26, 2014Assignee: Universitat de BarcelonaInventors: Ana María Grandas Sagarra, Albert Sánchez González, Enrique Pedroso Muller
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Publication number: 20140200338Abstract: This invention pertains to methods for oligonucleotide synthesis, specifically the synthesis of oligonucleotides that contain a high content of guanine monomers. In more detail, the invention relates to a method for coupling a nucleoside phosphoramidite during the synthesis of an oligonucleotide to a universal support, to a first nucleoside, or to an extending oligonucleotide. The invention further relates to oligonucleotides obtainable by the methods of the invention.Type: ApplicationFiled: October 15, 2013Publication date: July 17, 2014Applicant: CYTOS BIOTECHNOLOGY AGInventor: BRIAN STEPHEN SPROAT
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Patent number: 8765933Abstract: A process of stereoselectively synthesizing ?-nucleoside, e.g., 2?-deoxy-2,2?-difluorocytidine, is described. The process includes reacting a tetrahydrofuran compound of the following formula: in which wherein R1, R2, R3, R4, and L as defined in the specification, with a nucleobase derivative in the presence of an oxidizing agent.Type: GrantFiled: March 30, 2012Date of Patent: July 1, 2014Assignee: PharmaEssentia Corp.Inventors: Chungsun Chien, Pin-Shu Chien, Chan-Kou Hwang
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Publication number: 20140179875Abstract: Described herein are novel solid-supported sulfurization reagents having the general structure: (I) wherein (P) is a polymer; X is a linker; R1 is an alkyl group, a cycloalkyl group, an aryl group, or a heterocycle; and R2 is an alkyl group, an aryl group, a methyleneacyloxy group having the formula —CH2—O—C(O)—R7, a methylene carbonate group having the formula —CH2—O—C(O)—OR8, or a methylene carbamate group having the formula —CH2—O—C(O)—NR9R10, wherein R7 is a C1 to C20 hydrocarbon residue, R8 is any alkyl, cycloalkyl, aryl, or heteroaryl, and R9 and R10 are independently hydrogen, alkyl, cycloalkyl, aryl, or heteroaryl. Other embodiments include solid-supported sulfurization reagents having the structure of Formula I, wherein (P) is a polystyrene-based solid support and X is an aromatic linker. Also described herein are methods for synthesizing the solid-supported sulfurization reagents and their use during the synthesis of oligonucleotides.Type: ApplicationFiled: July 24, 2012Publication date: June 26, 2014Applicant: GIRINDUS AMERICA, INC.Inventors: Wieslaw Adam Mazur, Victor Sorokin, Steven Karl Laughlin
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Patent number: 8759508Abstract: The compounds are of class of chromophoric 1,2,3-triazolyl equipped silyl linking groups that are useful in the chemical synthesis of RNA.Type: GrantFiled: May 16, 2008Date of Patent: June 24, 2014Assignee: GE Healthcare Dharmacon, Inc.Inventor: Michael Oren Delaney
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Patent number: 8759509Abstract: A procedure for using thermolabile groups to protect a hydroxyl function, above all in nucleosides, nucleotides, oligomers, nucleic acids during the reactions of organic synthesis. Various new compounds that can be used to implement the procedure. The way of using thermolabile groups to protect hydroxyl functions consists in a primary, secondary and tertiary hydroxyl group converting into a groups during the reaction between a compound and a compound whose hydroxyl group is to be blocked. The blocking reaction is carried out by means of widely known methods appropriate for that purpose in the presence of a chemically basic catalyst. The obtained product has its hydroxyl group blocked. Then the compound with the group blocked can be used for the purposes of various chemical processes. After their completion, the hydroxyl group is unblocked by dissolving it in a solvent at a temperature of 50-95° C.Type: GrantFiled: June 1, 2011Date of Patent: June 24, 2014Assignee: Instytut Chemii Bioorganicznej Polskiej Akademii NaukInventor: Marcin Krzysztof Chmielewski
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Publication number: 20140142253Abstract: The thiol modified oligonucleotides have vast number of applications in the field of nucleic acid chemistry. The conjugates generated by mono thiol groups are unstable at higher temperature, in high salt concentration buffers and in presence other thiols. There is strong need to develop a novel thiol modifier probes that can generate multiple thiol groups. Described herein are efficient processes and compounds, dithiolane phosphoramidites derivative and dithiolane succinyl supports. The advantage of our cyclic disulfide thiol modifier is multifold a) each incorporation introduces two thiol groups; b) it can be introduced at any desired site of oligonucleotides; c) The symmetrical branching nature of the spacer in the linker arm of dithiolane allows for clean oligo synthesis, where cleavage of the linker arm and thereby of loss of oligo chain is prevented.Type: ApplicationFiled: October 28, 2013Publication date: May 22, 2014Applicant: ChemGenes CorporationInventors: Suresh C. Srivastava, Santhosh Kumar Thatikonda, Sant K. Srivastav, Praveen K. Shukla, Alok Srivastava
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Patent number: 8691970Abstract: An object of the present invention is to provide a useful and novel phosphoramidite compound for the synthesis of oligo-RNA. A phosphoramidite compound represented by general formula (1), wherein: BX represents a nucleobase optionally having a protecting group; and R1 is a substituent represented by general formula (2), wherein: R11, R12 and R13 are the same or different and each represents hydrogen or alkoxy; R2a and R2b are the same or different and each represents alkyl, or R2a and R2b taken together with the adjacent nitrogen atom may form a 5- to 6-membered saturated amino cyclic group, the amino cyclic group optionally having an oxygen or sulfur atom as a ring-composing member in addition to the adjacent nitrogen atom; and WG1 and WG2 are the same or different and each represents an electron-withdrawing group.Type: GrantFiled: August 25, 2005Date of Patent: April 8, 2014Assignee: Nippon Shinyaku Co., Ltd.Inventors: Tadaaki Ohgi, Kouichi Ishiyama, Yutaka Masutomi
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Patent number: 8691968Abstract: The present invention provides compositions, methods, and kits relating to the protection and deprotection of molecules comprising nucleophilic groups, such as the protection and deprotection of thermostable polymerases. Also provided are methods of performing nucleic acid amplification using polymerases protected according to the invention.Type: GrantFiled: July 2, 2009Date of Patent: April 8, 2014Assignee: Allelogic Biosciences CorporationInventors: Fei Mao, Xing Xin, Wai-Yee Leung
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Publication number: 20140066612Abstract: The invention relates to a process for deblocking substantially a blocked, detectably labeled oligonucleotide by contacting the blocked detectably labeled oligonucleotide with an effective amount of a nucleophilic amino compound under conditions that result in substantial deblocking of the oligonucleotide, thereby giving the substantially deblocked oligonucleotide.Type: ApplicationFiled: August 9, 2013Publication date: March 6, 2014Applicant: LIFE TECHNOLOGIES CORPORATIONInventors: Gulilat GEBEYEHU, Richard Pires
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Patent number: 8664357Abstract: According to the present invention, there is provided a process for the preparation of a first compound selected from peptides, oligonucleotides and peptide nucleic acids. The process comprises synthesizing the first compound and then separating the first compound formed in step (i) from a second compound, which is a reaction by-product of the synthesis of the first compound and/or an excess of a reagent used for the synthesis of a first compound by a process of diafiltration. The membrane used for the diafiltration process is stable in organic solvents and provides a rejection for the first compound which is greater than the rejection for the second compound.Type: GrantFiled: August 7, 2009Date of Patent: March 4, 2014Assignee: Imperial Innovations LimitedInventors: Andrew Guy Livingston, Ludmila Georgieva Peeva, Sheyung Wang Jerry So, Renato Campos Vasconceles, Robin John Leatherbarrow, Edward William Tate, Piers Robert James Gaffney
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Publication number: 20140051846Abstract: Disclosed are O-protected compounds of the formula (I): wherein B is an optionally protected nucleobase, and R1-R3 are as described herein, a method of preparing such compounds, and a method of preparing oligonucleotides such as RNA starting from such compounds. The O-protected compounds have one or more advantages, for example, the 2?-O-protected compound is stable during the various reaction steps involved in oligonucleotide synthesis; the protecting group can be easily removed after the synthesis of the oligonucleotide, for example, by reaction with tetrabutylammonium fluoride; and/or the O-protected groups do not generate DNA/RNA alkylating side products, which have been reported during removal of 2?-O-(2-cyanoethyl)oxymethyl or 2?-O-[2-(4-tolylsulfonyl)ethoxymethyl groups under similar conditions.Type: ApplicationFiled: March 29, 2012Publication date: February 20, 2014Applicant: TheUnited ofAmerica,asrepresentedbythe Secre -tary,Department ofHealthand Human ServiceInventors: Serge L. Beaucage, Jacek Cieslak
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Patent number: 8653254Abstract: There is a demand for a convenient production method of an NC type purine nucleoside. The present invention relates to a method of producing a purine nucleoside represented the formula (I?) or a salt thereof, which comprising reacting a pyrimidine nucleoside represented by the formula (I) or a salt thereof with a purine nucleobase represented by the formula B?H in the presence of a Lewis acid.Type: GrantFiled: March 30, 2010Date of Patent: February 18, 2014Assignee: Takeda Pharmaceutical Company LimitedInventors: Tadashi Umemoto, Yoji Hayase, Shumpei Murata, Kenichi Miyata
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Patent number: 8647821Abstract: Described are devices and methods for detecting binding on an electrode surface. In addition, devices and methods for electrochemically synthesizing polymers and devices and methods for synthesizing and detecting binding to the polymer on a common integrated device surface are described.Type: GrantFiled: December 22, 2012Date of Patent: February 11, 2014Assignee: Intel CorporationInventors: Hernan A. Castro, Gordon D. Holt, Brandon C. Barnett, Handong Li, Narayanan Sundararajan, Wei Wang
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Patent number: 8629263Abstract: Disclosed herein are nucleoside phosphoramidates and their use as agents for treating viral diseases. These compounds are inhibitors of RNA-dependent 5 RNA viral replication and are useful as inhibitors of HCV NS5B polymerase, as inhibitors of HCV replication and for treatment of hepatitis C infection in mammals.Type: GrantFiled: January 25, 2013Date of Patent: January 14, 2014Assignee: Gilead Pharmasset LLCInventors: Bruce Ross, Michael Joseph Sofia, Ganapati Reddy Pamulapati, Suguna Rachakonda, Hai-Ren Zhang, Byoung-Kwon Chun, Peiyuan Wang
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Patent number: 8614086Abstract: Described are quality control methods and devices for the reproducible manufacturing and integrity monitoring of polymers on electrochemical synthesis and detection chips. The devices and methods allow for simultaneous manufacturing and synthesis of polymers.Type: GrantFiled: December 28, 2006Date of Patent: December 24, 2013Assignee: Intel CorporationInventors: Gordon Holt, Ghadeer Antanius, Brandon Barnett
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Publication number: 20130317206Abstract: The present invention provides a solid-phase support for oligonucleotide synthesis for synthesizing long chain oligonucleotide, RNA oligonucleotide and modified oligonucleotide at high synthetic quantity and high purity with a low loading amount of a linker. Provided is a solid-phase support for oligonucleotide synthesis comprising a porous resin bead having a monovinyl monomer unit, a crosslinkable vinyl monomer unit and a polyethylene glycol unit and a cleavable linker loaded on its surface, the porous resin bead having a group capable of binding to a carboxy group by a dehydration condensation reaction on its surface, the cleavable linker having a carboxy group, wherein the carboxy group of the cleavable linker is bound to the group capable of binding to a carboxy group, by a dehydration condensation reaction, and a loading amount of the cleavable linker is 1 to 80 ?mol/g relative to the weight of the porous resin bead.Type: ApplicationFiled: May 23, 2013Publication date: November 28, 2013Inventors: Eri MAETA, Kenjiro MORI, Kazuya MIWA
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Patent number: 8569476Abstract: A method for preparing oligonucleotide comprising reacting the compound of Formula (1) with the compound of Formula (2) in a liquid reaction medium under the condition of condensation reaction to obtain the compound of formula (3) is provided. 1-(2-mesitylenesulfonyl)-3-nitro-1H-1,2,4-triazole (MSNT) is applied as condensing agent. Oligonucleotides synthesized in the liquid reaction medium could be obtained on a large scale.Type: GrantFiled: September 22, 2009Date of Patent: October 29, 2013Assignee: Suzhou Ribo Life Science Co., Ltd.Inventors: Zhen Xi, Jinyu Huang, Junbin Zhang
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Publication number: 20130267697Abstract: The present invention provides a protected nucleotide for elongation, which can be purified efficiently and in a high yield by a liquid-liquid extraction operation, and can achieve an oligonucleotide production method by a phosphoramidite method. It has been found that the above-mentioned problem can be solved by a particular oligonucleotide comprising a protected base and/or particular oligonucleotide protected by a branched chain-containing aromatic group at 3?-position.Type: ApplicationFiled: February 15, 2013Publication date: October 10, 2013Inventors: Kunihiro Hirai, Satoshi Katayama, Takayoshi Torii, Ryotaro Nakaya, Daisuke Takahashi
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Patent number: 8552174Abstract: Methods of deprotecting polynucleotides are disclosed. One aspect of the method of deprotecting polynucleotides, among others, includes: providing a polynucleotide, wherein the polynucleotide includes at least one nucleotide monomer that has at least one protecting group selected from the following: a base having a protecting group, a 2?-hydroxyl protecting group, and a combination thereof, and deprotecting at least one of the protecting groups of the polynucleotide by introducing the polynucleotide to a solution including an ?-effect nucleophile.Type: GrantFiled: March 23, 2006Date of Patent: October 8, 2013Assignees: Agilent Technologies, Inc., The Regents of the University of ColoradoInventors: Douglas J. Dellinger, Zoltan Timar, Agnieszka Sierzchala, Geraldine Dellinger, Marvin H. Caruthers, Joel Myerson
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Patent number: 8541569Abstract: The present invention provides building blocks and methods for synthesizing very pure RNA in a form that can efficiently be modified at the 3? end. Reverse RNA monomer phosphoramidites have been developed for RNA synthesis in 5??3? direction, leading to very clean oligo synthesis that allows for the introduction of various modifications at the 3?-end cleanly and efficiently. Higher coupling efficiency per step have been observed during automated oligo synthesis with the reverse RNA amidites disclosed herein, resulting in a greater ability to achieve higher purity and produce very long oligonucleotides. The use of the reverse RNA phosphoramidites in the synthetic process of this invention leads to oligonucleotides free of N+1 species.Type: GrantFiled: February 19, 2010Date of Patent: September 24, 2013Assignee: ChemGenes CorporationInventors: Suresh C. Srivastava, Naveen P. Srivastava
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Patent number: 8524882Abstract: The invention relates to a process for deblocking substantially a blocked, detectably labeled oligonucleotide by contacting the blocked detectably labeled oligonucleotide with an effective amount of a nucleophilic amino compound under conditions that result in substantial deblocking of the oligonucleotide, thereby giving the substantially deblocked oligonucleotide.Type: GrantFiled: June 3, 2011Date of Patent: September 3, 2013Assignee: Life Technologies CorporationInventors: Gulilat Gebeyehu, Richard Pires
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Publication number: 20130197209Abstract: The invention provides modified nucleotide or nucleoside molecule comprising a purine or pyrimidine base and a ribose or deoxyribose sugar moiety having a removable 3?-OH blocking group covalently attached thereto, such that the 3? carbon atom has attached a group of the structure —O—Z wherein Z is any of —C(R?)2-O—R?, —C(R?)2-N(R?)2, —C(R?)2-N(H)R?, —C(R?)2-S—R? and —C(R?)2-F, wherein each R? is or is part of a removable protecting group; each R? is independently a hydrogen atom, an alkyl, substituted alkyl, arylalkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocyclic, acyl, cyano, alkoxy, aryloxy, heteroaryloxy or amido group, or a detectable label attached through a linking group; or (R?)2 represents an alkylidene group of formula ?C(R??)2 wherein each R?? may be the same or different and is selected from the group comprising hydrogen and halogen atoms and alkyl groups; and wherein said molecule may be reacted to yield an intermediate in which each R? is exchanged for H or, where Z is —C(R?) 2-F, the F is eType: ApplicationFiled: March 8, 2013Publication date: August 1, 2013Applicant: ILLUMINA CAMBRIDGE LIMITEDInventors: John MILTON, Xiaolin Wu, Mark Smith, Joseph Brennan, Colin Bames, Xiaohai Liu, Silke Ruediger
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Publication number: 20130197208Abstract: The present invention provides massively parallel oligonucleotide synthesis and purification for applications that utilize large collections of defined high-fidelity oligonucleotides (e.g., from about 101 to about 105 different sequences, generally between 25-160 bases in length).Type: ApplicationFiled: November 20, 2012Publication date: August 1, 2013Applicant: Affymetrix, Inc.Inventor: Affymetrix, Inc.
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Publication number: 20130178612Abstract: Chiral auxiliaries useful for efficiently producing a phosphorus atom-modified nucleic acid derivative with high stereoregularity, and compounds represented by the following the general formula (I) or the general formula (XI) for introducing the chiral auxiliaries.Type: ApplicationFiled: September 22, 2011Publication date: July 11, 2013Applicant: CHIRALGEN, LTD.Inventors: Takeshi Wada, Mamoru Shimizu
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Publication number: 20130158248Abstract: The compounds of formula (I) substantially in exo form or salts thereof, wherein: X is a biradical selected from —(CH2)n—*, —(CH2CH2O)nCH2CH2—*, methylcyclohexyl and methylphenyl; n is an integer ranging between 1 and 30; Y is a radical selected from —COOH, a substituted phosphoramidite radical and N-hydroxysuccinimide ester (or other active ester) of carboxylic acid; and * represents the place through which X binds to Y, are useful in a general process for solid-phase preparation of maleimide-oligonucleotide derivatives.Type: ApplicationFiled: May 2, 2011Publication date: June 20, 2013Applicant: UNIVERSITAT DE BARCELONAInventors: Ana María Grandas Sagarra, Albert Sánchez González, Enrique Pedroso Muller
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Publication number: 20130137861Abstract: A reagent for oligonucleotide synthesis or purification, wherein the reagent has a structure of: X—C-L-H??(Formula A) wherein X is a phosphoramidite group, an H-phosphonate group, an acetal group, or an isocyanate; C is a direct bond or a cleavable adaptor represented by —Ca-Cb—; L is a hydrocarbyl chain; and H is a terminal alkyne or an activated cyclooctyne. The reagent of Formula (A) can be used in the synthesis and purification of oligonucleotides.Type: ApplicationFiled: November 6, 2012Publication date: May 30, 2013Applicant: AGILENT TECHNOLOGIES, INC.Inventor: Agilent Technologies, Inc.
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Patent number: 8445734Abstract: The present invention discloses novel and improved nucleosidic and nucleotidic compounds that are useful in the light-directed synthesis of oligonucleotides, as well as, methods and reagents for their preparation. These compounds are characterized by novel photolabile protective groups that are attached to either the 5?- or the 3?-hydroxyl group of a nucleoside moiety. The photolabile protective group is comprised of a 2-(2-nitrophenyl)-ethyoxycarbonyl skeleton with at least one substituent on the aromatic ring that is either an aryl, an aroyl, a heteroaryl or an alkoxycarbonyl group. The present invention includes the use of the aforementioned compounds in light-directed oligonucleotide synthesis, the respective assembly of nucleic acid microarrays and their application.Type: GrantFiled: June 2, 2010Date of Patent: May 21, 2013Assignee: NIGU Chemie GmbHInventors: Sigrid Buehler, Markus Ott, Wolfgang Pfleiderer
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Publication number: 20130123486Abstract: This invention describes reagent precursors and methods for chemical and biochemical reactions. These reagent precursors that can be activated in solution upon irradiation to generate reagents required for the subsequent chemical reactions. Specifically, photogenerated reagents (PGR) are useful for controlling parallel combinatorial synthesis and various chemical and biochemical reactions.Type: ApplicationFiled: November 16, 2011Publication date: May 16, 2013Inventor: Xiaolian GAO
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Publication number: 20130122507Abstract: The present invention provides a method for amplification of a target nucleic acid sequence or signal, wherein an amplification reaction mixture is used which contains at least one reversibly modified oligonucleotide having a non-hydroxyl group 3? end which can be converted into a hydroxyl 3? end upon exposure to a chemical and/or irradiation and/or a range of temperature. The present invention also provides a reversibly modified oligonucleotide as described above, and a nucleic acid amplification reaction mixture and kit comprising such an oligonucleotide.Type: ApplicationFiled: November 20, 2012Publication date: May 16, 2013Inventor: Wanli Bi