Abstract: The present invention provides novel, regioselectively-acylated oligosaccharide compounds and methods for preparing them. In another aspect, the invention provides a method for preparing a selectively-acylated oligosaccharide. The method includes forming a reaction mixture containing a protected oligosaccharide and an acylating agent. The protected oligosaccharide includes at least three hydroxyl moieties and each hydroxyl moiety is protected with a silyl protecting group. The reaction mixture is formed under conditions sufficient to selectively replace at least one silyl protecting group with a —C(0)-C1_6 alkyl group, and the selectively-acylated oligosaccharide comprises at least one —C(0)-C1_6 alkyl group and at least one silyl protecting group.

Abstract: The present invention provides novel, regioselectively-acylated oligosaccharide compounds and methods for preparing them. In another aspect, the. invention provides a method for preparing a selectively-acylated oligosaccharide. The method includes forming a reaction mixture containing a protected oligosaccharide and an acylating agent. The protected oligosaccharide includes at least three hydroxyl moieties and each hydroxyl moiety is protected with a silyl protecting group. The reaction mixture is formed under conditions sufficient to selectively replace at least one silyl protecting group with a —C(0)-C1_6 alkyl group, and the selectively-acylated oligosaccharide comprises at least one —C(0)-C1_6 alkyl group and at least one silyl protecting group.

Abstract: The present invention provides novel, regioselectively-acylated oligosaccharide compounds and methods for preparing them. In another aspect, the. invention provides a method for preparing a selectively-acylated oligosaccharide. The method includes forming a reaction mixture containing a protected oligosaccharide and an acylating agent. The protected oligosaccharide includes at least three hydroxyl moieties and each hydroxyl moiety is protected with a silyl protecting group. The reaction mixture is formed under conditions sufficient to selectively replace at least one silyl protecting group with a —C(0)-C1_6 alkyl group, and the selectively-acylated oligosaccharide comprises at least one —C(0)-C1_6 alkyl group and at least one silyl protecting group.

Abstract: The present invention provides a one-pot method of preparing an unprotected ?-O-glycolipid. The first step involves contacting a protected ?-iodo sugar with a catalyst and a lipid comprising a hydroxy group, under conditions sufficient to prepare a protected ?-O-glycolipid. The second step involves deprotecting the protected ?-O-glycolipid under conditions sufficient to prepare the unprotected ?-O-glycolipid, wherein the contacting and deprotecting steps are performed in a single vessel. The present invention also provides a one-pot method of preparing an unprotected ?-O-glycolipid following the steps for the preparation of the unprotected ?-O-glycolipid.

Abstract: The present invention provides novel, regioselectively-acylated oligosaccharide compounds and methods for preparing them. In another aspect, the. invention provides a method for preparing a selectively-acylated oligosaccharide. The method includes forming a reaction mixture containing a protected oligosaccharide and an acylating agent. The protected oligosaccharide includes at least three hydroxyl moieties and each hydroxyl moiety is protected with a silyl protecting group. The reaction mixture is formed under conditions sufficient to selectively replace at least one silyl protecting group with a —C(0)-C1_6 alkyl group, and the selectively-acylated oligosaccharide comprises at least one —C(0)-C1_6 alkyl group and at least one silyl protecting group.

Abstract: The present invention provides for a practical, universal and efficient method to ligate two large macromolecules (e.g., proteins) using the alkyne-azide 1,3-dipolar cycloaddition reaction to produce a conjugated macromolecule, such as a multivalent scFv. The present invention also provides for conjugate macromolecules comprising a plurality of macromolecule components cross-linked through at least one linking group comprising at least one 1,2,3-triazole moiety, wherein at least 50 percent of the macromolecule components in the conjugate macromolecule has only one site available for cross-linking.

Abstract: The present invention provides a one-pot method of preparing an unprotected ?-O-glycolipid. The first step involves contacting a protected ?-iodo sugar with a catalyst and a lipid comprising a hydroxy group, under conditions sufficient to prepare a protected ?-O-glycolipid. The second step involves deprotecting the protected ?-O-glycolipid under conditions sufficient to prepare the unprotected ?-O-glycolipid, wherein the contacting and deprotecting steps are performed in a single vessel. The present invention also provides a one-pot method of preparing an unprotected ?-O-glycolipid following the steps for the preparation of the unprotected ?-O-glycolipid.

Abstract: The present invention provides a one-pot method of preparing an unprotected ?-O-glycolipid. The first step involves contacting a protected ?-iodo sugar with a catalyst and a lipid comprising a hydroxy group, under conditions sufficient to prepare a protected ?-O-glycolipid. The second step involves deprotecting the protected ?-O-glycolipid under conditions sufficient to prepare the unprotected ?-O-glycolipid, wherein the contacting and deprotecting steps are performed in a single vessel. The present invention also provides a one-pot method of preparing an unprotected ?-O-glycolipid following the steps for the preparation of the unprotected ?-O-glycolipid.

Abstract: The present invention provides a one-pot method of preparing an unprotected ?-O-glycolipid. The first step involves contacting a protected ?-iodo sugar with a catalyst and a lipid comprising a hydroxy group, under conditions sufficient to prepare a protected ?-O-glycolipid. The second step involves deprotecting the protected ?-O-glycolipid under conditions sufficient to prepare the unprotected ?-O-glycolipid, wherein the contacting and deprotecting steps are performed in a single vessel. The present invention also provides a one-pot method of preparing an unprotected ?-O-glycolipid following the steps for the preparation of the unprotected ?-O-glycolipid.

Abstract: The present invention provides for a practical, universal and efficient method to ligate two large macromolecules (e.g., proteins) using the alkyne-azide 1,3-dipolar cycloaddition reaction to produce a conjugated macromolecule, such as a multivalent scFv. The present invention also provides for conjugate macromolecules comprising a plurality of macromolecule components cross-linked through at least one linking group comprising at least one 1,2,3-triazole moiety, wherein at least 50 percent of the macromolecule components in the conjugate macromolecule has only one site available for cross-linking.

Abstract: This invention provides labeled-substrate conjugates for assaying enzymes, particularly neuraminidases. Also provided are assays that are useful for identifying compounds that inhibit sialyltransferases or neuraminidases and may be useful in treating subjects with influenza. In particular, the present invention relates to methods of using such labeled substrate conjugates to screen for enzyme inhibitors, particularly in a high-throughput format.

Abstract: A method for the production of a-O-galactosyl ceramide precursor is demonstrated. The method involves the reaction of galactosyl iodide with a sphingosine derivative or phytosphingosine derivative in the presence of a quaternary ammonium iodide salt to prepare the a-O-galactosyl ceramide precursor in the a-anomer form. The a-O-galactosyl ceramide is then prepared by reaction with a suitable fatty acid or fatty acid derivative.

Abstract: This invention provides labeled-substrate conjugates for assaying enzymes, particularly neuraminidases. Also provided are assays that are useful for identifying compounds that inhibit sialyltransferases or neuraminidases and may be useful in treating subjects with influenza. In particular, the present invention relates to methods of using such labeled substrate conjugates to screen for enzyme inhibitors, particularly in a high-throughput format.

Abstract: The present invention provides novel disulfone compounds and methods of preparing and using those compounds to further prepare biologically relevant gem-disulfone analogs of natural enzyme substrates. Methods of using a variety of disulfone compounds as reagents capable of forming symmetrical and non-symmetrical &agr;, &bgr; unsaturated gem-disulfones are also provided. There is also provided a disulfone reagent which reacts with both aromatic and aliphatic aldehydes in good to moderate yield to give exclusively the trans isomer. In accordance with further aspects of the present invention, a methodology for stereospecifically preparing potential gem-disulfone enzyme inhibitors is provided. A synthetic design which allows easy substitution of functional groups so that a number of substrate analogs can be synthesized readily is also provided.