Phosphoryl group differentiating alpha-amino acids from beta- and gamma-amino acids in prebiotic peptide formation

doi:10.1002/qua.10562

	Phosphoryl group differentiating alpha-amino acids from beta- and gamma-amino acids in prebiotic peptide formation
	Jiang, Y; Tan, B ; Chen, ZZ ; Liu, T ; Zhong, RG ; Li, YM ; Stewart, DJ ; Zhao, YF ; Jiang, HL
刊名	INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY
	2003-09-05
卷号	94 期号:4 页码:232-241
关键词	alpha-amino acids beta-amino acids pentacoordinate phosphorous origin of life peptide
ISSN号	0020-7608
DOI	10.1002/qua.10562
文献子类	Article
英文摘要	in 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.
WOS关键词	N-PHOSPHOAMINO ACIDS
WOS研究方向	Chemistry ; Mathematics ; Physics
语种	英语
出版者	JOHN WILEY & SONS INC
WOS记录号	WOS:000184632700006
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/274186]
专题	中国科学院上海药物研究所
通讯作者	Zhao, YF
作者单位	1.Xiamen Univ, Dept Chem, Xiamen 361005, Fujian, Peoples R China 2.Tsing Hua Univ, Dept Chem, Sch Life Sci & Engn, Minist Educ,Key Lab Bioorgan Phosphorous Chem, Beijing 100084, Peoples R China 3.Chinese Acad Sci, Shanghai Inst Biol Sci, Shanghai Inst Mat Med, State Key Lab New Drug Res,Ctr Drug Discovery & D, Shanghai 200031, Peoples R China
推荐引用方式 GB/T 7714	Jiang, Y,Tan, B,Chen, ZZ,et al. Phosphoryl group differentiating alpha-amino acids from beta- and gamma-amino acids in prebiotic peptide formation[J]. INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY,2003,94(4):232-241.
APA	Jiang, Y.,Tan, B.,Chen, ZZ.,Liu, T.,Zhong, RG.,...&Jiang, HL.(2003).Phosphoryl group differentiating alpha-amino acids from beta- and gamma-amino acids in prebiotic peptide formation.INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY,94(4),232-241.
MLA	Jiang, Y,et al."Phosphoryl group differentiating alpha-amino acids from beta- and gamma-amino acids in prebiotic peptide formation".INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY 94.4(2003):232-241.