Synthesis of S-linked glycosyl amino acids in aqueous solution with unprotected carbohydrates.
[figure: see text] The cyclic sulfamidate 5 was synthesized in 60% overall yield from L-serine benzyl ester. Compound 5 reacted cleanly with the sodium thiolate salt of a variety of unprotected 1-thio sugars in aqueous buffer to afford the corresponding S-linked amino acid glycoconjugates in good yields after hydrolysis of the N-sulfates.
Cohen
S B
SB
Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215, USA.
Halcomb
R L
RL
D000596:Amino Acids / Q000138:chemical synthesis*; D002241:Carbohydrates / Q000737:chemistry*; D006001:Glycoconjugates / Q000138:chemical synthesis*; D012996:Solutions; D013449:Sulfonamides / Q000138:chemical synthesis
D000596:Amino Acids; D002241:Carbohydrates; D006001:Glycoconjugates; D012996:Solutions; D013449:Sulfonamides