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Synthesis of Muramyl Peptides Containing meso-Diaminopimelic Acid

✍ Scribed by Niels Kubasch; Richard R. Schmidt

Publisher
John Wiley and Sons
Year
2002
Tongue
English
Weight
352 KB
Volume
2002
Category
Article
ISSN
1434-193X

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✦ Synopsis

Chain-extension of L-glutamate aldehyde 3 by means of the Wittig-Horner reaction furnished the desired C 7 dicarboxylic acid derivative, which in turn, after C-C double bond hydrogenation and protecting group manipulation, afforded the 2,6-diaminopimelic acid derivatives (S,R)-9 and (S,S)-9, both with the desired orthogonal protecting group pattern. Synthesis of the muramic acid derivative 15 and attachment of an L-alanine residue furnished muramyl-L-alanine 18. The corresponding 1,6-anhydromuramic acid derivative 26 was obtained similarly. Treatment of these compounds with peptides 28-30 and with the 2,6-diaminopimelic acid containing di-and tripeptides 32a, 32b, and 35 gave the protected mura- [a

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