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rdf:type |
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lifeskim:mentions |
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pubmed:issue |
6
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pubmed:dateCreated |
2007-3-9
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pubmed:abstractText |
With the hope of mimicking the chemical and biological properties of natural 3-O-methylmannose-containing polysaccharides (MMPs), synthetic 3-O-methylmannose-containing polysaccharides (sMMPs) were designed and synthesized in a convergent manner. With little modification of the Mukaiyama glycosidation, high alpha-selectivity (>50:1 approximately >20:1) and yields (79 approximately 74%) were achieved for the key glycosidation steps. The exceptionally high alpha-selectivity observed was shown to be consequent to the selective anomerization of beta- to alpha-anomer under the glycosidation conditions. This glycosidation is well suited for a highly convergent oligosaccharide synthesis, particularly because of excellent chemical yields even when using approximately equal-sized donors and acceptors in an approximately 1:1 molar ratio. An iterative reaction sequence allowed the growing oligosaccharide to double in size after each cycle and led to an efficient synthesis of sMMP 8-, 12-, and 16-mers 18-20.
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pubmed:grant |
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pubmed:commentsCorrections |
http://linkedlifedata.com/resource/pubmed/commentcorrection/17274657,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17274657-1112801,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17274657-14245425,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17274657-14966891,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17274657-15127453,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17274657-15889182,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17274657-16536536,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17274657-3558356,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17274657-4429968,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17274657-4515612,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17274657-4633353,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17274657-4743516,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17274657-4855991,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17274657-5166559,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17274657-5276305,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17274657-5679967,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17274657-6706966,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17274657-6706967,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17274657-7061496,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17274657-856790,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17274657-9621108
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pubmed:language |
eng
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pubmed:journal |
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pubmed:citationSubset |
IM
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pubmed:chemical |
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pubmed:status |
MEDLINE
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pubmed:month |
Mar
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pubmed:issn |
0022-3263
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pubmed:author |
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pubmed:issnType |
Print
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pubmed:day |
16
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pubmed:volume |
72
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
1931-40
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pubmed:dateRevised |
2009-11-18
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pubmed:meshHeading |
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pubmed:year |
2007
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pubmed:articleTitle |
Synthetic 3-O-methylmannose-containing polysaccharides (sMMPs): design and synthesis.
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pubmed:affiliation |
Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
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pubmed:publicationType |
Journal Article,
Research Support, N.I.H., Extramural
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