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rdf:type | |
lifeskim:mentions | |
pubmed:dateCreated |
1988-3-15
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pubmed:abstractText |
O-alpha-D-Mannopyranosyl-(1----6)-O-beta-D-mannopyranosyl-(1----4)-O-(2- acetamido-2-deoxy-beta-D-glucopyranosyl)-(1----4)-2-acetamido-2-deoxy- D-glucopyranose was isolated from bovine or ovine mannosidosis urine. After peracetylation, treatment with trimethylsilyl trifluoromethanesulfonate gave a high yield of a peracetyl oxazoline, which was phosphorylated with dibenzyl phosphate to give a dibenzyl glycosyl phosphate that was converted into a peracetyl tetrasaccharide phosphate by catalytic hydrogenolysis. A coupling reaction with P1-dolichyl P2-diphenyl diphosphate, prepared in two stages from pig-liver dolichol, yielded a peracetyl diphosphoric diester, which on O-deacetylation gave P1-dolichyl P2-[O-alpha-D-mannopyranosyl-(1----6)-O-beta-D-mannopyranosyl-(1----4)-O -(2- acetamido-2-deoxy-beta-D-glucopyranosyl)-(1----4)-2-acetamido-2-deoxy- alpha-D- glucopyranosyl] diphosphate. This tetrasaccharide lipid intermediate was active as an acceptor of D-mannose residues from GDP-D-mannose in the presence of calf pancreas microsomes.
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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 |
Nov
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pubmed:issn |
0008-6215
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:day |
15
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pubmed:volume |
169
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
221-33
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pubmed:dateRevised |
2007-11-14
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pubmed:meshHeading |
pubmed-meshheading:3427586-Acetylation,
pubmed-meshheading:3427586-Animals,
pubmed-meshheading:3427586-Carbohydrate Conformation,
pubmed-meshheading:3427586-Carbohydrate Sequence,
pubmed-meshheading:3427586-Dolichol Phosphates,
pubmed-meshheading:3427586-Indicators and Reagents,
pubmed-meshheading:3427586-Liver,
pubmed-meshheading:3427586-Magnetic Resonance Spectroscopy,
pubmed-meshheading:3427586-Oligosaccharides,
pubmed-meshheading:3427586-Optical Rotation,
pubmed-meshheading:3427586-Polyisoprenyl Phosphate Sugars,
pubmed-meshheading:3427586-Swine
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pubmed:year |
1987
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pubmed:articleTitle |
Synthesis of the tetrasaccharide lipid intermediate P1-dolichyl P2-[O-alpha-D-mannopyranosyl-(1----6)-O-beta-D-mannopyranosyl-(1----4) -O-(2- acetamido-2-deoxy-beta-D-glucopyranosyl)-(1----4)-2-acetamido-2- deoxy-alpha-D-glucopyranosyl] diphosphate.
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pubmed:affiliation |
Department of Biological Chemistry, Harvard Medical School, Boston, Massachusetts.
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pubmed:publicationType |
Journal Article,
Research Support, U.S. Gov't, P.H.S.,
Research Support, U.S. Gov't, Non-P.H.S.
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