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
Synthesis and biological activity of some lipophilic derivatives of 1-thio-muramoyl-l-alanyl-d-isoglutamine
โ Scribed by Akira Hasegawa; Eiji Seki; Yuichi Hioki; Makoto Kiso; Ichiro Azuma
- Publisher
- Elsevier Science
- Year
- 1984
- Tongue
- English
- Weight
- 686 KB
- Volume
- 131
- Category
- Article
- ISSN
- 0008-6215
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โฆ Synopsis
2-N-Octadecanoyl derivatives of 1-S-acetyl-, 1-S-octadecanoyl-, and of 6-O-octadecanoyl-1-S-octadecanoyl-1-thiomuramoyl-L-ala nyl-D-isoglutamine were synthesized from benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-(octadecanoylamino)-beta-D-glucopy ran oside. Their immunoadjuvant activities were examined in guinea-pigs.
๐ SIMILAR VOLUMES
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
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.-
In our continuing efforts to elucidate the relationships between the biological activities of iv-acetylmuramoyl-L-alanyl-D-isoglutamine\*\* (MDP) and the structure of the carbohydrate moiety, and to obtain glycopeptide adjuvants that exhibit strong activity and lower toxicity, it was demonstrated th
N-Acetylmuramoyl-L-alanyl-D-isoglutamine (MDP), a fragment of bacterial peptidoglycan, is capable of replacing whole mycobacteria in complete Freund's adjuvant'. In the course of our investigation of the relationship between the chemical structure and biological activities of MDP, it has been reveal