Synthesis of a new allosamidin analog, N,N'-diacetyl-beta-chitobiosyl allosamizoline and its inhibitory activity against some chitinases

H Terayama; H Kuzuhara; S Takahashi; S Sakuda; Y Yamada

doi:10.1271/bbb.57.2067

Synthesis of a new allosamidin analog, N,N'-diacetyl-beta-chitobiosyl allosamizoline and its inhibitory activity against some chitinases

Biosci Biotechnol Biochem. 1993 Dec;57(12):2067-9. doi: 10.1271/bbb.57.2067.

Authors

H Terayama¹, H Kuzuhara, S Takahashi, S Sakuda, Y Yamada

Affiliation

¹ Institute of Physical and Chemical Research (RIKEN), Saitama, Japan.

PMID: 7764363
DOI: 10.1271/bbb.57.2067

Abstract

A new allosamidin analog (2), possessing an N',N'-diacetylchitobiosyl moiety as a constituent, was stereoselectively synthesized through the coupling reaction between the disaccharide thioglycoside derivative (5) and allosamizoline derivative (6). The inhibitory activity of 2 against chitinases derived from an insect, yeast and mold were tested and compared with that of allosamidin (1).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetylglucosamine / analogs & derivatives*
Acetylglucosamine / chemical synthesis
Acetylglucosamine / pharmacology
Animals
Bombyx / enzymology
Carbohydrate Sequence
Chitinases / antagonists & inhibitors*
Molecular Conformation
Molecular Sequence Data
Saccharomyces cerevisiae / enzymology
Trichoderma / enzymology
Trisaccharides / chemical synthesis*
Trisaccharides / pharmacology

Substances

Trisaccharides
N,N'-diacetylchitobiosyl allosamizoline
Chitinases
Acetylglucosamine