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
Synthesis and immunoadjuvant activity of 2,2′-O-[2,2′-diacetamido-2,3,2′,3′-tetradeoxy-6,6′-di-O-(2-tetradecyl-hexadecanoyl)-α, α′-trahalose-3,3′-diyl]bis(N-d-lactoyl-l-alanyl-d-isoglutamine)
✍ Scribed by Hideharu Ishida; Yasuyuki Imai; Makoto Kiso; Akira Hasegawa; Takuma Sakurai; Ichiro Azuma
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- English
- Weight
- 640 KB
- Volume
- 195
- Category
- Article
- ISSN
- 0008-6215
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✦ Synopsis
The disaccharide of 6-O-(2-tetradecylhexadecanoyl)muramoyl dipeptide coupled through an alpha-(1----1)-alpha linkage, named in the title, and an analog bearing a single peptide moiety, have been synthesized from 2,2'-diazido-2,2'-dideoxy-alpha,alpha'-trehalose. The immunoadjuvant activities of the products were examined.
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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
The title glycosides were synthesised from D-glUCOSe, via the common intermediate methyl 2-acetamido-4-O-benzoyld-bromo-2,3,6-trideoxy-a-D-ribohexopyranoside . \*To whom enquiries should be addressed. \*\*The overall efficiency of this procedure can be improved by using a phase-transfer process' in
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