| Chemo-Enzymatic Synthesis of Each Enantiomer of Orthogonally-Protected 4,4-Difluoroglutamic Acid - A Candidate Monomer for Chiral Brønsted-Acid Peptide-Based Catalysts. | |
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MedLine Citation:
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PMID: 22039908 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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We have accomplished an asymmetric synthesis of each independent enantiomer of 4,4-difluoroglutamic acid. This alpha-amino acid has been of interest in medicinal chemistry circles. Key features of the synthesis include highly scalable procedures, a Reformatsky-based coupling reaction, and straightforward functional group manipulations to make the parent amino acid. Enantioenrichment derives from an enzymatic resolution of the synthetic material. Conversion of the optically enriched compounds to differentially protected forms allows selective formation of peptide bonds. 4,4- Difluoroglutamic acid, in a suitably protected form, is also shown to exhibit enhanced catalytic activity in both an oxidation reaction and a reduction reaction, in comparison to the analogous glutamic acid derivative. |
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Authors:
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Yang Li; Scott J Miller |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2011-10-31 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: - ISSN: 1520-6904 ISO Abbreviation: - Publication Date: 2011 Oct |
Date Detail:
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Created Date: 2011-11-1 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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