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Phosphoryl group differentiating α‐amino acids from β‐ and γ‐amino acids in prebiotic peptide formation
Author(s) -
Jiang Yang,
Tan Bo,
Chen ZhongZhou,
Liu Tong,
Zhong RuGang,
Li YanMei,
Stewart David Jeremy,
Zhao YuFen,
Jiang HuaLiang
Publication year - 2003
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.10562
Subject(s) - chemistry , alanine , amino acid , peptide , stereochemistry , intramolecular force , density functional theory , computational chemistry , biochemistry
In recent years β‐amino acids have increased their importance enormously in defining secondary structures of β‐peptides. Interest in β‐amino acids raises the question: Why and how did nature choose α‐amino acids for the central role in life? In this article we present experimental results of MS and 31 P NMR methods on the chemical behavior of N ‐phosphorylated α‐alanine, β‐alanine, and γ‐amino butyric acid in different solvents. N ‐Phosphoryl α‐alanine can self‐assemble to N ‐phosphopeptides either in water or in organic solvents, while no assembly was observed for β‐ or γ‐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 α‐alanine (2a–c), with five‐membered ring, and five isomers of IMCPA derived from β‐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 α‐alanine. Both experimental and theoretical studies indicate that the structural difference among α‐, β‐, and γ‐amino acids can be recognized by formation of IMCPA after N ‐phosphorylation. © 2003 Wiley Periodicals, Inc. Int J Quantum Chem 94: 232–241, 2003

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