| Synthetic 6-O-methylglucose-containing polysaccharides (sMGPs): design and synthesis. | |
| | |
MedLine Citation:
|
PMID: 17274656 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
|
With the hope of mimicking the chemical and biological properties of natural 6-O-methyl-D-glucose-containing polysaccharides (MGPs), synthetic 6-O-methyl-D-glucose-containing polysaccharides (sMGPs) were designed and synthesized from alpha-, beta-, and gamma-cyclodextrins (CDs). The synthetic route proved to be flexible and general, to furnish a series of sMGPs ranging from 6-mer to 20-mer. A practical and scalable method was discovered selectively to cleave the CD derivatives and furnish the linear precursors to the glycosyl donors and acceptors. The Mukaiyama glycosidation was adopted to couple the glycosyl donors with the glycosyl acceptors. Unlike in the 3-O-methyl-D-mannose-containing polysaccharide (sMMP) series, the amount of the Mukaiyama acid required in the sMGP series increased with an increase of substrate size; that is, for large oligomers, more than one equivalent of the acid was required. |
| | |
Authors:
|
Malte Meppen; Yonghui Wang; Hwan-Sung Cheon; Yoshito Kishi |
Related Documents
:
|
6816596 - Somatic antigens of pseudomonas aeruginosa. the structure of o-specific polysaccharide ... 15923126 - Structural characterization of lipoarabinomannans from mycobacterium tuberculosis and m... 6438066 - Chemical and immunological characterization of lipopolysaccharides from phase i and pha... 6163716 - Immunochemical characterization of brucella lipopolysaccharides and polysaccharides. 7374176 - Aconitine-induced writhing as a method for assessing aspirin-like analgesic activity. 12182676 - Synthesis of cyclic peptidomimetics from aldol building blocks. |
Publication Detail:
|
Type: Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't Date: 2007-02-03 |
Journal Detail:
|
Title: The Journal of organic chemistry Volume: 72 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2007 Mar |
Date Detail:
|
Created Date: 2007-03-09 Completed Date: 2007-05-31 Revised Date: 2009-11-18 |
Medline Journal Info:
|
Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
|
Languages: eng Pagination: 1941-50 Citation Subset: IM |
Affiliation:
|
Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA. |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
|
Cyclodextrins
/
chemistry Drug Design Glycosylation Methylglucosides / chemistry* Molecular Mimicry Oligosaccharides / chemical synthesis Polysaccharides / chemical synthesis* |
| Grant Support | |
ID/Acronym/Agency:
|
NS 12108/NS/NINDS NIH HHS; R01 NS012108-25/NS/NINDS NIH HHS |
| Chemical | |
Reg. No./Substance:
|
0/Cyclodextrins; 0/Methylglucosides; 0/Oligosaccharides; 0/Polysaccharides; 2461-70-3/6-O-methylglucose |
| Comments/Corrections | |
Erratum In:
|
J Org Chem. 2007 May 25;72(11):4292 |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
Previous Document: Enantioselective quenching of room-temperature phosphorescence lifetimes of proteins: bovine and hum...
Next Document: Synthetic 3-O-methylmannose-containing polysaccharides (sMMPs): design and synthesis.