Synthesis of (N-acetyl-1-O-acylmuramoyl)-l-alanyl-d-isoglutamines, and their immunoadjuvant activities
โ Scribed by Akira Hasegawa; Yuichi Hioki; Makoto Kiso; Ichiro Azuma
- Publisher
- Elsevier Science
- Year
- 1983
- Tongue
- English
- Weight
- 476 KB
- Volume
- 123
- Category
- Article
- ISSN
- 0008-6215
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โฆ Synopsis
I-0-Acyl derivatives of N-acetylmuramoyl-I.-alanyl-n-isogtutaminc (MDP) have been synthesized from 2-acctamido-l-O-bcnzoyl-4.6-O-isopropylidenc-3-0-[D-I-(methoxycarbonyI)ethyl]-e-D-glucopyranose. Their immunoadjuvant activities were examined in guinea-pigs.
(N-ACETYL-I -0-ACYLMURAMOYI.).L-AI.ANYI.-I)-TSOGI.UTAMINES 71 methylene), 1730 and 1260 (ester), 1710 (C=O), and 1650 and 1530 cm-' (amide).
๐ SIMILAR VOLUMES
Our synthetic studies on muramyl peptides have significantly elucidated the relationship between the immunoadjuvant activity and the chemical structure. 2)
O-(N-Acetyl-~-muramyl-L-alanyl-D\_isoglutamine)-(1~4)-~-acetyl-D-glucosamine (3, the re--peating disaccharide dipeptTde unit %tained by endo-&acetylglucos%minidase lysis of bacterial cell walls, has been synthesized in a twelve-step sequence from g-acetyl-g-glucosamine.
N-Acetyl-1-thiomuramoyl-L-alanyl-D-isoglutamine and some lipophilic analogs were synthesized from benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-[D-1-(methoxycarbonyl)ethyl ]- alpha-D-glucopyranoside (1). O-Debenzoylation of 2, derived from 1 by oxidation, gave 2-acetamido-2-deoxy-4,6-O-isoprop
Title compound 1 was synthesized by a published route which had to be modified (seven steps from readily obtainable starting materials). Characterization of 1 was achieved by spectroscopic means (FAB-MS, ' H-NMR, including 2D-COSY). Furthermore, commercially available reference material purchased fo