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dc.contributor.authorJiang, Y
dc.contributor.authorTan, B
dc.contributor.authorChen, ZZ
dc.contributor.authorLiu, T
dc.contributor.authorZhong, RG
dc.contributor.authorLi, YM
dc.contributor.authorStewart, DJ
dc.contributor.authorZhao, YF
dc.contributor.author赵玉芬
dc.contributor.authorJiang, HL
dc.date.accessioned2012-04-19T01:08:20Z
dc.date.available2012-04-19T01:08:20Z
dc.date.issued2003-06-30
dc.identifier.citationINTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY,2003,94(4):232-241zh_CN
dc.identifier.issn0020-7608
dc.identifier.urihttp://dx.doi.org/doi:10.1002/qua.10562
dc.identifier.urihttps://dspace.xmu.edu.cn/handle/2288/12117
dc.description.abstractin recent years beta-amino acids have increased their importance enormously in defining secondary structures of beta-peptides. Interest in beta-amino acids raises the question: Why and how did nature choose alpha-amino acids for the central role in life? In this article we present experimental results of MS and P-31 NMR methods on the chemical behavior of N-phosphorylated alpha-alanine, beta-alanine, and gamma-amino butyric acid in different solvents. N-Phosphoryl alpha-alanine can self-assemble to N-phosphopeptides either in water or in organic solvents, while no assembly was observed for beta- or gamma-amino acids. An intramolecular carboxylic-phosphoric mixed anhydride (IMCPA) is the key structure responsible for their chemical behaviors. Relative energies and solvent effects of three isomers of IMCPA derived from alpha-alanine (2a-c), with five-membered ring, and five isomers of IMCPA derived from beta-alanine (4a-e), with six-membered ring, were calculated with density functional theory at the B3LYP/6-31G** level. The lower relative energy (3.2 kcal/mol in water) of 2b and lower energy barrier for its formation (16.7 kcal/mol in water) are responsible for the peptide formation from N-phosphoryl alpha-alanine. Both experimental and theoretical studies indicate that the structural difference among alpha-, beta-, and gamma-amino acids can be recognized by formation of IMCPA after N-phosphorylation. (C) 2003 Wiley Periodicals, Inc.zh_CN
dc.language.isoenzh_CN
dc.publisherJOHN WILEY & SONS INCzh_CN
dc.subjectalpha-amino acidszh_CN
dc.subjectbeta-amino acidszh_CN
dc.subjectpentacoordinate phosphorouszh_CN
dc.subjectorigin of lifezh_CN
dc.subjectpeptidezh_CN
dc.titlePhosphoryl group differentiating alpha-amino acids from beta- and gamma-amino acids in prebiotic peptide formationzh_CN
dc.typeArticlezh_CN


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