| Synthesis and chemical behaviour of D-glucosyl esters of glutamic acid having the side-chain carboxyl group involved in the glycosidic linkage. | |
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MedLine Citation:
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PMID: 1268876 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Simultaneous and stepwise deprotection of the fully benzylated D-glucosyl esters of 1-benzyl N-benzyloxycarbonyl- and N-tert-butyloxycarbonyl-L-glutamic acid (1 and 5, respectively) have been examined. Catalytic hydrogenation of 1 led to intramolecular aminolysis to give pyroglutamic acid and D-glucose, but similar treatment in the presence of trifluoroacetic acid afforded both anomers of 1-O-(L-gamma-glutamyl)-D-glucopyranose, which were characterized as trifluoroacetates (2alpha and 2beta) and converted into 2,3,4,6-tetra-O-acetyl-1-O-[1-methyl N-(acetyl)-L-glutam-5-oyl]-D-glucopyranose (4) which was also prepared by a definitive method. Hydrogenolysis of 5 gave both anomers of 1-O-[N-(tert-butyloxycarbonyl)-L-gamma-glutamyl]-D-glucopyranose (6), which, upon treatment with trifluoroacetic acid at - 10 degrees, afforded 2alpha and 2beta, respectively. The structure of 6beta was established by its conversion into 2,3,4,6-tetra-O-acetyl-1-O-[1-methyl N-(tert-butyloxycarbonyl)-L-glutam-5-oyl]-beta-D-glucopyranose (7beta), whereas similar treatment of 6alpha gave a mixture of 1,3,4,6-tetra-O-acetyl-2-O-[1-methyl N-(tert-butyloxycarbonyl)-L-glutam-5-oyl]-alpha-D-glucopyranose (9) and 7alpha. A 1 leads to 2 acyl migration occurred during esterification of the aglycon carboxyl group of 6alpha with diazomethane to give 2-O-[1-methyl N-(tert-butyloxycarbonyl)-L-glutam-5-oyl]-alpha-D-glucopyranose (8). |
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Authors:
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D Keglević; J Horvat; F Plavsić |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Carbohydrate research Volume: 47 ISSN: 0008-6215 ISO Abbreviation: Carbohydr. Res. Publication Date: 1976 Mar |
Date Detail:
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Created Date: 1976-08-02 Completed Date: 1976-08-02 Revised Date: 2008-11-21 |
Medline Journal Info:
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Nlm Unique ID: 0043535 Medline TA: Carbohydr Res Country: NETHERLANDS |
Other Details:
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Languages: eng Pagination: 49-61 Citation Subset: IM |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Chemical Phenomena Chemistry Glucosides* / chemical synthesis Glutamates* Glycosides* / chemical synthesis Magnetic Resonance Spectroscopy Methods Optical Rotation Structure-Activity Relationship |
| Chemical | |
Reg. No./Substance:
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0/Glucosides; 0/Glutamates; 0/Glycosides |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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