Quantitation in the regioselectivity of acylation of glycosyl diglycerides: total synthesis of a Streptococcus pneumoniae alpha-glucosyl diglyceride

The fidelity of acylation regioselectivity in the synthesis of mixed glycosyl diacylglycerols can be accurately measured by quantitative C-13 NMR spectroscopy using a 1-C-13-labelled fatty acid and a paramagnetic relaxation enhancement agent. Exquisite regioselectivity is achieved using a stepwise a...

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 53; no. 6; pp. 1100 - 1103
Main Authors Richardson, Mark B., Smith, Dylan G. M., Williams, Spencer J.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2017
Subjects
Acylation
Chemistry
Chemistry, Multidisciplinary
Diglycerides
Fatty acids
NMR spectroscopy
Physical Sciences
Pneumonia
Science & Technology
Streptococcus
Streptococcus pneumoniae
Synthesis
LACTOBACILLUS-PLANTARUM
BACTERIA
STRUCTURAL ELUCIDATION
RECOGNITION
MINCLE
POSITIONAL ISOMERS
KILLER T-CELLS
ANTIGENS
GLYCOLIPIDS
DIACYLGLYCERIDES
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Summary:The fidelity of acylation regioselectivity in the synthesis of mixed glycosyl diacylglycerols can be accurately measured by quantitative C-13 NMR spectroscopy using a 1-C-13-labelled fatty acid and a paramagnetic relaxation enhancement agent. Exquisite regioselectivity is achieved using a stepwise acylation/substitution of a glycosyl beta-bromohydrin, which is applied to the total synthesis of Streptococcus pneumoniae Glc-DAG-s2.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1359-7345
1364-548X
DOI:10.1039/c6cc09584d