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Synthesis and evaluation of diastereoisomeric alkylating pseudo-disaccharides as potential affinity reagents for trehalase

✍ Scribed by Edith Bar-Guilloux; Jacques Defaye; Jochen Lehmann; Robert Nardin; Daniel Robic; Klaus Urbahns

Book ID: 102992818
Publisher: Elsevier Science
Year: 1993
Tongue: English
Weight: 529 KB
Volume: 250
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(93)84149-z

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✦ Synopsis

Reaction of (k )-(3/4,5,6)-4-bromo-5,6-epoxy-3-hydroxycyclohexene with 2,3,4,6-tetra-O-acetyl-lthioiu-o-glucopyranose, followed by treatment of the resulting isolated diastereoisomeric 4-bromo-3,5dihydroxycyclohexene 1-thioglycoside derivatives with base under phase-transfer conditions, gave (R)and (3)_(3,4,6/5)-3,4-epoxy-6-S_(l-thioa-~-glucopyranosyl)-5-hydro~cyclohexene.

None of them was substrate or inhibitor for cockchafer trehalase.

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