Abstract: The present disclosure relates to synthetic glycolipids of the formula (I): wherein • A represents (CH2)n with n being an integer from 2 to 10 or CH2—CH2—[O—CH2—CH2]m with m being an integer from 1 to 5; • B represents NR3 or OCH2, with R3 representing H, Me, Et or n-Pr; • “Sugar” represents formulas (A) or (B) where R1 represents OH and R2 represents H, or where R1 represents H and R2 represents OH; • Y represents H when X and Z which are identical represent O—(CH2)p-CH3, or Z represents H when X and Y which are identical represent O—(CH2)p—CH3, with p being an integer from 5 to 18. Glycoliposomes comprising the synthetic glycolipids can be used for the delivery of a therapeutic or diagnostic agent to the central nervous system. Glycoliposomes comprising the synthetic glycolipids can be used to treat a CNS-related disease or disorder.

Abstract: Carbohydrate of Formula (A) where R1 is H and n an integer from 1 to 5, is synthesized by reacting, under heating, compound (A0) with HO—(CH2)n—CH?CH2 in the presence of an acid capable of liberating a proton, and cooling the reaction mixture to obtain a cooled mixture comprising compound (A). Carbohydrate of Formula (AAPG) where R2 is a monovalent protecting group, PG is a divalent protecting group and n an integer from 1 to 5, is synthesized by reacting, in the presence of a metal-containing zeolite, compound of Formula (APG) with compound of Formula (A1) where X is —I, —Br, —Cl, —CN, —OTf (Triflate), —OMs (Mesylate), —OTs (Tosylate), methylsulfate, or trichloroacetimidate. Deprotection of compound (AAPG) forms compound (AA) Carbohydrates (A) and (AA) can be coupled with a thiolated linker to form glycoconjugate precursors, which in turn are conjugatable with a carrier material such as a protein, peptide or polypeptide.

Abstract: Neoglycoconjugates as immunogens and therapeutic/diagnostic tools are described herein. The neoglycoconjugates are produced by conjugating a carbohydrate antigen intermediate to a free amine group of a carrier material (e.g., carrier protein). The intermediate comprises a linker having a first end and a second end, the first end being conjugated to a carbohydrate antigen via a thio ether bond and the second end comprising a functional group reactable with a free amine group. Following coupling, the carbohydrate antigen becomes covalently bound to the carrier material via an amide, a carbamate, a sulfonamide, a urea, or a thiourea bond, thereby producing the neoglycoconjugate. Applications of the neoglycoconjugates as antigens, immunogens, vaccines, and in diagnostics are also described.

Abstract: Neoglycoconjugates as immunogens and therapeutic/diagnostic tools are described herein. The neoglycoconjugates are produced by conjugating a carbohydrate antigen intermediate to a free amine group of a carrier material (e.g., carrier protein). The intermediate comprises a linker having a first end and a second end, the first end being conjugated to a carbohydrate antigen via a thio ether bond and the second end comprising a functional group reactable with a free amine group. Following coupling, the carbohydrate antigen becomes covalently bound to the carrier material via an amide, a carbamate, a sulfonamide, a urea, or a thiourea bond, thereby producing the neoglycoconjugate. Applications of the neoglycoconjugates as antigens, immunogens, vaccines, and in diagnostics are also described.

Abstract: The present description relates to glycoconjugates, glycoconjugate immunogens and glycoconjugate vaccines comprising carbohydrate antigens coupled to immunogenic carrier proteins, or materials used for detection and screening of resulting antibodies. Improved methods of more directly and precisely conjugating carbohydrate antigens to free thiol groups of immunogenic carrier proteins are described, including “click-chemistry” approaches based on photocatalytic thiol-ene reactions.