| Synthesis of histidinoalanine (HAL): a comparison of beta-lactone and sulfamidate electrophiles. | |
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MedLine Citation:
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PMID: 21612224 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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Previous syntheses of histidinoalanine (HAL) have led to mixtures of regioisomers and/or stereoisomers. For example, opening of N-Cbz-D-serine-beta-lactone (6) with Boc-L-His-OMe (5) gave a 2:1 mixture of tau- and pi-regioisomers. The sulfamidate 10, derived from N-benzyl-D-serine methyl ester (11), was reacted with Boc-L-His-OMe (5) to give the tau-HAL derivative 17 as a single isomer in 57% yield. A similarly prepared tau-HAL 19, bearing protecting groups that were all hydrogenolytically labile, led the free bis-amino acid, tau-L-histidinyl-D-alanine (tau-4), as a salt-free standard for amino acid analysis. |
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Authors:
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Carol M Taylor; Samanthi Thabrew De Silva |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2011-5-25 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: - ISSN: 1520-6904 ISO Abbreviation: - Publication Date: 2011 May |
Date Detail:
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Created Date: 2011-5-26 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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