Synthesis of 1′,6′-disubstituted sucroses and their behavior as glucosyl donors for a microbial α-glucosyltransferase
✍ Scribed by Hiroyuki Kakinuma; Hideya Yuasa; Hironobu Hashimoto
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- English
- Weight
- 670 KB
- Volume
- 284
- Category
- Article
- ISSN
- 0008-6215
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✦ Synopsis
Versatile 6'-chloro-6'-deoxy-1'-substituted sucrose derivatives were synthesized in search of an optimum donor substrate for the intermolecular transglucosylation with the alpha-glucosyltransferase from Protaminobacter rubrum. Two substituents at the C-1' and C-6' positions of sucrose were introduced utilizing the distinct reactivity of the corresponding sulfonates. Methyl beta-D-arabinofuranoside was most efficiently glucosylated with the 1'-deoxy derivative 5. Hydroxyl and fluoro groups at C-1' show a tendency to enhance the intramolecular transglucosylations, giving 3-O-(alpha-D-glucopyranosyl)-D-fructose derivatives.