DC Field | Value | Language |
---|---|---|
dc.contributor.author | Lee, Hee-Seung | ko |
dc.contributor.author | Park, JS | ko |
dc.contributor.author | Kim, BM | ko |
dc.contributor.author | Gellman, SH | ko |
dc.date.accessioned | 2013-03-04T16:24:53Z | - |
dc.date.available | 2013-03-04T16:24:53Z | - |
dc.date.created | 2012-02-06 | - |
dc.date.created | 2012-02-06 | - |
dc.date.issued | 2003-02 | - |
dc.identifier.citation | JOURNAL OF ORGANIC CHEMISTRY, v.68, no.4, pp.1575 - 1578 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.uri | http://hdl.handle.net/10203/83261 | - |
dc.description.abstract | We report a practical and scalable synthetic route for the preparation of alpha-substituted beta-amino acids (beta(2)-amino acids). Michael addition of a chiral hydroxylamine, derived from alpha-methylbenzylamine, to an alpha-alkylacrylate followed by cyclization gives a diastereomeric mixture of alpha-substituted isoxazolidinones. These diastereomers are separable by column chromatography. Subsequent hydrogenation of the purified isoxazolidinones followed by Fmoc protection affords enantiomerically pure Fmoc-beta(2)-amino acids, which are useful for beta-peptide synthesis. This route provides access to both enantiomers of a protected beta(2)-amino acid. | - |
dc.language | English | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.subject | BETA-AMINO ACIDS | - |
dc.subject | PROTEINOGENIC SIDE-CHAINS | - |
dc.subject | SOLID-PHASE SYNTHESIS | - |
dc.subject | ENANTIOSELECTIVE SYNTHESIS | - |
dc.subject | AQUEOUS-SOLUTION | - |
dc.subject | ASYMMETRIC-SYNTHESIS | - |
dc.subject | PEPTIDES | - |
dc.subject | FOLDAMERS | - |
dc.subject | OLIGOMERS | - |
dc.subject | RESIDUES | - |
dc.title | Efficient synthesis of enantionmerically pure beta(2)-amino acids via chiral isoxazolidinones | - |
dc.type | Article | - |
dc.identifier.wosid | 000181061700054 | - |
dc.identifier.scopusid | 2-s2.0-0242515860 | - |
dc.type.rims | ART | - |
dc.citation.volume | 68 | - |
dc.citation.issue | 4 | - |
dc.citation.beginningpage | 1575 | - |
dc.citation.endingpage | 1578 | - |
dc.citation.publicationname | JOURNAL OF ORGANIC CHEMISTRY | - |
dc.identifier.doi | 10.1021/jo026738b | - |
dc.contributor.localauthor | Lee, Hee-Seung | - |
dc.contributor.nonIdAuthor | Park, JS | - |
dc.contributor.nonIdAuthor | Kim, BM | - |
dc.contributor.nonIdAuthor | Gellman, SH | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordPlus | BETA-AMINO ACIDS | - |
dc.subject.keywordPlus | PROTEINOGENIC SIDE-CHAINS | - |
dc.subject.keywordPlus | SOLID-PHASE SYNTHESIS | - |
dc.subject.keywordPlus | ENANTIOSELECTIVE SYNTHESIS | - |
dc.subject.keywordPlus | AQUEOUS-SOLUTION | - |
dc.subject.keywordPlus | ASYMMETRIC-SYNTHESIS | - |
dc.subject.keywordPlus | PEPTIDES | - |
dc.subject.keywordPlus | FOLDAMERS | - |
dc.subject.keywordPlus | OLIGOMERS | - |
dc.subject.keywordPlus | RESIDUES | - |
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.