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Strong Aphicidal Activity of GlcNAc(β1→4)Glc Disaccharides: Synthesis, Physiological Effects, and Chitinase Inhibition
Author(s) -
Dussouy Christophe,
Bultel Laurent,
Saguez Julien,
Cherqui Anas,
Khelifa Mounia,
Grand Eric,
Giordanengo Philippe,
Kovensky José
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201200887
Subject(s) - chitinase , chemistry , aphid , stereoselectivity , stereochemistry , enzyme , chitin , biochemistry , biology , botany , catalysis , chitosan
The synthesis of four GlcNAc(β1→4)Glc disaccharides containing 2‐ O ‐acetyl and/or 6‐sulfate groups was performed in high yields with total 1,2‐ trans stereoselectivity. These disaccharides were evaluated as candidates for insect chitinase inhibition and aphicidal activity. All the compounds prepared displayed physiological effects on M. persicae aphids; however, the inhibition of chitinases of different sources (bacteria, fungus, and aphid) followed different patterns according to subtle structural characteristics.