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Synthesis ofN-(Glucopyranosid-3-yl)-D- and -L-alanyl-D-isoglutamine and Related Glycodipeptides

✍ Scribed by Calvo-Mateo, Ana ;De Las Heras, Federico G.

Publisher: John Wiley and Sons
Year: 1987
Tongue: English
Weight: 401 KB
Volume: 1987
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.198719870866

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✦ Synopsis

Six glucodipeptides, in which the D-laCtyl-L-Hhyl residue of the immunoadjuvant myramyl dipeptide is replaced by D-AI~I. ~-Ala. and GI y, have been synthesized. Coupling of benzyl 2-acetamido-4,6-0-bcnzylidcnc-3-[R-( I-carboxycthy1)amino-. -3-( l-carboxyethyl)ainino-, and ~carboxymethyl)amino]-23-dideoxy-cw-u-glucopyranosides 8,9. and 10. respectively, with r>-isogluiamine methyl ester and D-glutamine methyl ester rollowed by hydrogenolysis afforded the corresponding N-(2-acetamido-2,3-dideoxy-~gluccrpyrdnosid-3-yl) derivatives of ~-Ala-~-isoGln-OMe (14). L-Aln-o-isoGln-OMe (15), Gly-~-isoGln-OMe (I@, ~-A l a -~-G l n -OMe (20). t-Ala-D-Gln-OMe (21), and Gly-o-Gln-OMe (22).

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