Stereoconversion of Amino Acids and Peptides in Uryl-Pendant Binol Schiff Bases
DC Field | Value | Language |
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dc.contributor.author | Park, Hyunjung | - |
dc.contributor.author | Nandhakumar, Raju | - |
dc.contributor.author | Hong, Jooyeon | - |
dc.contributor.author | Ham, Sihyun | - |
dc.contributor.author | Chin, Jik | - |
dc.contributor.author | Kim, Kwan Mook | - |
dc.date.available | 2021-02-22T15:01:22Z | - |
dc.date.issued | 2008-10 | - |
dc.identifier.issn | 0947-6539 | - |
dc.identifier.issn | 1521-3765 | - |
dc.identifier.uri | https://scholarworks.sookmyung.ac.kr/handle/2020.sw.sookmyung/14584 | - |
dc.description.abstract | (S)-2-Hydroxy-2'-(3-phenyl-uryl-benzyl)-1,1'-binaphthyl-3-carboxal- dehyde (1) forms Schiff bases with a wide range of nonderivatized amino acids, including unnatural ones. Multiple hydrogen bonds, including resonance-assisted ones, fix the whole orientation of the imine and provoke structural rigidity around the imine C=N bond. Due to the structural difference and the increase in acidity of the cc proton of the amino acid, the imine formed with an L-amino acid (1-L-aa) is converted into the imine of the Damino acid (1-D-aa), with a D/L ratio of more than 10 for most amino acids at equilibrium. N-terminal amino acids in dipeptides are also predominantly epimerized to the D form upon imine formation with 1. Density functional theory calculations show that 1-D-Ala is more stable than 1-L-Ala by 1.64 kcal mol(-1), a value that is in qualitative agreement with the experimental result. Deuterium exchange of the alpha proton of alanine in the imine form was studied by H-1 NMR spectroscopy and the results support a stepwise mechanism in the L-into-D conversion rather than a concerted one; that is, de-protonation and protonation take place in a sequential manner. The deprotonation rate of L-Ala is approximately 16 times faster than that Of D-Ala. The protonation step, however, appears to favor L-amino acid production, which prevents a much higher predominance of the D form in the imine. Receptor I and the predominantly D-form amino acid can be recovered from the imine by simple extraction under acidic conditions. Hence, I is a useful auxiliary to produce D-amino acids of industrial interest by the conversion of naturally occurring L-amino acids or relatively easily obtainable racemic amino acids. | - |
dc.format.extent | 8 | - |
dc.language | 영어 | - |
dc.language.iso | ENG | - |
dc.publisher | WILEY-V C H VERLAG GMBH | - |
dc.title | Stereoconversion of Amino Acids and Peptides in Uryl-Pendant Binol Schiff Bases | - |
dc.type | Article | - |
dc.publisher.location | 독일 | - |
dc.identifier.doi | 10.1002/chem.200801036 | - |
dc.identifier.scopusid | 2-s2.0-55449112158 | - |
dc.identifier.wosid | 000261074800017 | - |
dc.identifier.bibliographicCitation | CHEMISTRY-A EUROPEAN JOURNAL, v.14, no.32, pp 9935 - 9942 | - |
dc.citation.title | CHEMISTRY-A EUROPEAN JOURNAL | - |
dc.citation.volume | 14 | - |
dc.citation.number | 32 | - |
dc.citation.startPage | 9935 | - |
dc.citation.endPage | 9942 | - |
dc.type.docType | Article | - |
dc.description.isOpenAccess | N | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
dc.relation.journalResearchArea | Chemistry | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Multidisciplinary | - |
dc.subject.keywordPlus | SERINE RACEMASE | - |
dc.subject.keywordPlus | RECOGNITION | - |
dc.subject.keywordPlus | ALCOHOLS | - |
dc.subject.keywordPlus | RESOLUTION | - |
dc.subject.keywordPlus | DIPEPTIDE | - |
dc.subject.keywordPlus | MODELS | - |
dc.subject.keywordPlus | ORGANOCATALYSTS | - |
dc.subject.keywordPlus | THERMOCHEMISTRY | - |
dc.subject.keywordPlus | RECEPTORS | - |
dc.subject.keywordPlus | COMPLEX | - |
dc.subject.keywordAuthor | amino acids | - |
dc.subject.keywordAuthor | chiral auxiliaries | - |
dc.subject.keywordAuthor | epimerization | - |
dc.subject.keywordAuthor | Schiff bases | - |
dc.identifier.url | https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.200801036 | - |
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