ISSN:
0170-2041
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Synthese von N-(Glucopyranosid-3-yl)-D- und -L-alanyl-D-isoglutamin und verwandten GlycodipeptidenEs wurden sechs Glucodipeptide dargestellt, bei denen der D-Lactyl-L-alanyl-Rest des immunoadjuvanten Muramyldipeptids durch D-Ala, L-Ala und Gly ersetzt wurde. Die Kupplungsreaktion von Benzyl-2-acetamido-4,6-O -benzylidene-3-[R-(1-carboxyethyl)amino]-2,3-dideoxy-α-D-glucopyranosid 8, 9 bzw. 10 mit D-Isoglutamin-methylester und D-Glutamin-methylester und nachfolgende Hydrogenolyse ergab die entsprechenden N-(2-Acetamino-2,3-dideoxy-D-glucopyranosid-3-yl)-Derivate von D-Ala-D-iso-Gln-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) und Gly-D-Gln-OMe (22).
Notes:
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).
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.198719870866
