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Synthesis of acyclic analogs ofN-acetylmuramyl-L-alanyl-D-isoglutamine (MDP)

✍ Scribed by Danklmaier, Johann ;Hünig, Helmut

Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
665 KB
Volume
1990
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The syntheses of the acyclic MDP analogs 27–37 is described, the carbohydrate moiety of muramic acid being replaced by acyclic amino alcohol structures. Their preparation was accomplished by hydrolytic cleavage of the cyclic, disubstituted 3‐morpholinones 2–5 and protection of the free amino group to give the compounds 6–9. Coupling with the dipeptide L‐alanyl‐D‐isoglutamine benzyl ester, cleavage of the N‐protecting group, acylation with acyl chains of various lengths and hydrogenation produced the title compounds 27–37. The latter exhibit variable lipophilic character.

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