Our synthetic studies on muramyl peptides have significantly elucidated the relationship between the immunoadjuvant activity and the chemical structure. 2)
Bacterial cell wall constituents. II.1 synthesis of O-(N-acetyl-β-muramyl-L-alanyl-D-isoglutamine)-(1→4)-N-acetyl-D-glucosamine
✍ Scribed by Philippe L. Durette; Eric P. Meitzner; T.Y. Shen
- Publisher
- Elsevier Science
- Year
- 1979
- Tongue
- French
- Weight
- 228 KB
- Volume
- 20
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
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.
📜 SIMILAR VOLUMES
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.-
Spacer arms 2.1-3.7 nm (21-37 A) long were prepared, and coupled with the methyl P-glycoside of ~-acetylmuramyl-L-alanyl-D-isoglutamine benzyl ester, to give blocked 6acylates. Deprotection was effected with palladium chloride and triethylsilane. Chemical conjugates of MDP-meningococcal group C poly
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