Muramyl Dipeptide Derivatives with Multiprenylacetyl Group. Synthesis and Immunological Activities
- 1 November 1981
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 54 (11) , 3530-3535
- https://doi.org/10.1246/bcsj.54.3530
Abstract
Several linear and branched all-trans-multiprenylacetic acids were synthesised, and introduced to the 6 position of the sugar moiety of muramyl dipeptide and its analog, via an amino acid as a linking unit. Compared with the saturated stearoyl derivative, all the compounds having a multiprenylacetyl group exhibited more potent adjuvant activity on the induction of delayed-type hypersensitivity to N-acetyl-3-(4-arsonophenylazo)-l-tyrosine. The derivatives with larger branched side chains tended to have increased activity.Keywords
This publication has 9 references indexed in Scilit:
- Synthesis of immunologically active muramyl dipeptide derivatives containing a quinonyl moiety via aminoacyl intermediates.CHEMICAL & PHARMACEUTICAL BULLETIN, 1981
- Synthesis of Lipophilic Muramyl Dipeptide Derivatives via O-Aminoacyl IntermediatesBulletin of the Chemical Society of Japan, 1980
- Synthetic immunostimulants derived from the bacterial cell wallJournal of Medicinal Chemistry, 1980
- Novel quinonyl derivatives of muramyl dipeptide possessing potent antitumor activity.CHEMICAL & PHARMACEUTICAL BULLETIN, 1979
- Synthesis of 6-O-Mycoloyl-Nacetylmuramyl-l-alanyl-d-isoglutamine with Antitumor ActivityBulletin of the Chemical Society of Japan, 1978
- Vaccination of Experimental Monkeys Against Plasmodium falciparum : A Possible Safe AdjuvantScience, 1978
- Minimal structural requirements for adjuvant activity of bacterial peptidoglycan derivativesBiochemical and Biophysical Research Communications, 1974
- The use of N-hydroxy-5-norbornene-2,3-dicarboximide acitive esters in peptide synthesis.CHEMICAL & PHARMACEUTICAL BULLETIN, 1974