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Synthesis of N ‐(Glucopyranosid‐3‐yl)‐ D ‐ and ‐ L ‐alanyl‐ D ‐isoglutamine and Related Glycodipeptides
Author(s) -
CalvoMateo Ana,
De Las Heras Federico G.
Publication year - 1987
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198719870866
Subject(s) - chemistry , dipeptide , hydrogenolysis , immunoadjuvant , stereochemistry , glutamine , residue (chemistry) , amino acid , biochemistry , catalysis , adjuvant , medicine
Six glucodipeptides, in which the D ‐lactyl‐ L ‐alanyl residue of the immunoadjuvant myramyl dipeptide is replaced by D ‐Ala, L ‐Ala, and Gly, have been synthesized. Coupling of benzyl 2‐acetamido‐4,6‐O‐benzylidene‐3‐[ R ‐(1‐carboxyethyl)amino‐, ‐ S ‐(1‐carboxyethyl)amino‐, and ‐(carboxymethyl)amino]‐2,3‐dideoxy‐α‐ D ‐glucopyranosides 8,9 , and 10 , respectively, with D ‐isoglutamine methyl ester and D ‐glutamine methyl ester followed by hydrogenolysis afforded the corresponding N ‐(2‐acetamido‐2,3‐dideoxy‐ D ‐glucopyranosid‐3‐yl) derivatives of D ‐Ala‐ D ‐isoGln‐OMe ( 14 ), L ‐Ala‐ D ‐isoGln‐OMe ( 15 ), Gly‐ D ‐isoGln‐OMe ( 16 ), D ‐Ala‐ D ‐Gln‐OMe ( 20 ), L ‐Ala‐ D ‐Gln‐OMe ( 21 ), and Gly‐ D ‐OMe ( 22 ).