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- W2051282635 abstract "Chain-extension of L-glutamate aldehyde 3 by means of the Wittig−Horner reaction furnished the desired C7 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 muramyl peptides 17, 37, 40, 42, 44, 46, and 49a and 49b, which, after deprotection, afforded the desired target molecules muramyl-L-alanine (38), muramyl-L-alanyl-D-glutamic acid (39), muramyl-L-alanyl-D-glutaminide (41), muramyl-L-alanyl-D-isoglutaminyl-L-lysine (43), muramyl-L-alanyl-D-isoglutaminyl-(2S,6R)-2,6-diaminopimelic acid (45), muramyl-L-alanylL-isoglutaminyl-(2S,6R)-2,6-diaminopimelinyl-D-alanine (47), 1,6-anhydromuramyl-L-alanyl-D-isoglutaminyl-(2S,6R)-2,6-diaminopimelic acid (50a), and 1,6-anhydromuramyl-L-alanyl-D-isoglutaminyl-(2S,6S)-2,6-diaminiopimelic acid (50b). (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)" @default.
- W2051282635 created "2016-06-24" @default.
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- W2051282635 date "2002-08-01" @default.
- W2051282635 modified "2023-09-24" @default.
- W2051282635 title "Synthesis of Muramyl Peptides Containing meso-Diaminopimelic Acid" @default.
- W2051282635 doi "https://doi.org/10.1002/1099-0690(200208)2002:16<2710::aid-ejoc2710>3.0.co;2-8" @default.
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