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Predicate | Object |
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
2
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pubmed:dateCreated |
1989-3-2
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pubmed:abstractText |
Synthesis of the title compound provides a prochiral, glycosyl-donor substrate well suited for use as a probe of the catalytic functioning of D-glucosyl-mobilizing enzymes, because the full stereochemistry of enzymic reactions at its double bond may be unambiguously determined by examining the reaction products. The starting material for the synthesis was 2,6-anhydro-D-glycero-D-gulo-heptonic acid, from which 3,7-anhydro-4,5,6,8-tetra-O-benzyl-1-deoxy-D-glycero-D-gulo-2- octulose was prepared in eight steps. Reduction with lithium aluminum deuteride, and conversion of the resulting diastereomeric alcohols into (Z)-3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,2-dideoxy-2-deuterio-D- gluco-oct-2-enitol (11) and 3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,2-dideoxy-2-deuterio-D- glycero-D-gulo-oct-1-enitol (16), was carried out. By-products were 3,7-anhydro-2-O-benzoyl-4,5,6,8-tetra-O-benzyl-1,2-dideoxy-2-deuterio -D-erythro-L-galacto-octitol and 3,7-anhydro-2-O-benzoyl-4,5,6,8-tetra-O-benzyl-1,2-dideoxy-2-deuterio -D-erythro-L-talo-octitol, which could, like compound 16, be recycled. On debenzylation the oct-2-enitol 11 yielded (Z)-3,7-anhydro-1,2-dideoxy-2-deuterio-D-gluco-oct-2-enitol.
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pubmed:grant | |
pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical | |
pubmed:status |
MEDLINE
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pubmed:month |
Dec
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pubmed:issn |
0008-6215
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:day |
1
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pubmed:volume |
183
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
287-99
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pubmed:dateRevised |
2008-11-21
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pubmed:meshHeading |
pubmed-meshheading:3214843-Acetylation,
pubmed-meshheading:3214843-Carbohydrate Conformation,
pubmed-meshheading:3214843-Catalysis,
pubmed-meshheading:3214843-Chemical Phenomena,
pubmed-meshheading:3214843-Chemistry,
pubmed-meshheading:3214843-Glycoside Hydrolases,
pubmed-meshheading:3214843-Glycosylation,
pubmed-meshheading:3214843-Magnetic Resonance Spectroscopy,
pubmed-meshheading:3214843-Molecular Structure,
pubmed-meshheading:3214843-Stereoisomerism,
pubmed-meshheading:3214843-Sugar Alcohols
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pubmed:year |
1988
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pubmed:articleTitle |
Synthesis of (Z)-3,7-anhydro-1,2-dideoxy-2-deuterio-D-gluco-oct-2- enitol, a prochiral substrate for probing the catalytic functioning of of glucosylases.
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pubmed:affiliation |
Institut für Organische Chemie und Biochemie, Universität Freiburg i. Br., West Germany.
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pubmed:publicationType |
Journal Article,
Research Support, U.S. Gov't, P.H.S.,
Research Support, Non-U.S. Gov't
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