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SYNTHESES OF 4'-DEOXY-ALPHA-MALTOSYL FLUORIDE AND 4''-DEOXY-ALPHA-MALTOTRIOSYL FLUORIDE AS PROBES OF ALPHA-GLUCANOTRANSFERASE MECHANISMS

TitleSYNTHESES OF 4'-DEOXY-ALPHA-MALTOSYL FLUORIDE AND 4''-DEOXY-ALPHA-MALTOTRIOSYL FLUORIDE AS PROBES OF ALPHA-GLUCANOTRANSFERASE MECHANISMS
Publication TypeJournal Article
Year of Publication1995
AuthorsLINDHORST, TK, BRAUN, C, Withers, SG
JournalCARBOHYDRATE RESEARCH
Volume268
Pagination93-106
Date PublishedMAR 1
ISSN0008-6215
Abstract

4'-Deoxy-alpha-maltosyl fluoride and 4''-deoxy-alpha-maltotriosyl fluoride were synthesized to serve as mechanistic probes for alpha-glucanotransferases such as the glycogen debranching enzyme. The deoxy derivatives were prepared starting from maltose and maltotriose, respectively. Deoxygenation of the terminal 4-hydroxyl group was accomplished by radical reduction of the iodo sugar formed after iodide displacement of the corresponding protected triflate. The anomeric fluoride was introduced by treatment of the protected hemiacetal with diethylaminosulfur trifluoride, predominantly giving the beta-anomeric product. Conversion to the alpha anomer was achieved using HF . pyridine.

DOI10.1016/0008-6215(94)00317-9