Stereochemical effect of the amino acid side chain on the formation of penta-coordinate phosphorus intermediates from N-phosphorylamino acids:: A theoretical study

被引：0
|
作者：
Zhao Li-Jiao [1 ]
Zhong Ru-Gang
Zhen Yan
Zhao Yu-Fen
机构：
[1] Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100022, Peoples R China
[2] Tsinghua Univ, Dept Chem, Minist Educ, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Beijing 100084, Peoples R China
来源：
ACTA CHIMICA SINICA | 2006年 / 64卷 / 09期
关键词：
N-phosphorylamino acid; origin of life; stereochemical effect; DFT;
D O I：
暂无
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The stereochemical effect of the chiral amino acid residues on the formation of penta-coordinate phosphorus intermolecular mixed carboxylic-phosphoric anhydride (IMCPA) from N-phosphorylamino acids was studied with density functional theory (DFIP) calculations at B3LYP/6-311G(d,p) level. The reaction pathways for the formation of penta-coordinate phosphorus intermediates with different configurations through the carboxyl oxygen on amino acid group attacking the phosphoryl group from different directions were simulated and the stereoselectivity in the formation of IMCPA was discussed.
引用
收藏
页码：959 / 962
页数：4
相关论文
共 25 条
  • [11] LI YM, 1992, INT J PEPT PROT RES, V39, P375
  • [12] Penta-coordinate phosphorous compounds and biochemistry
    Lin, CX
    Li, YM
    Cheng, CM
    Han, B
    Wan, R
    Feng, YB
    Zhao, YF
    [J]. SCIENCE IN CHINA SERIES B-CHEMISTRY, 2002, 45 (04): : 337 - 348
  • [13] The origin of life - a review of facts and speculations
    Orgel, LE
    [J]. TRENDS IN BIOCHEMICAL SCIENCES, 1998, 23 (12) : 491 - 495
  • [14] ORIGIN OF LIFE - FACING UP TO THE PHYSICAL SETTING
    PACE, NR
    [J]. CELL, 1991, 65 (04) : 531 - 533
  • [15] Peng CY, 1996, J COMPUT CHEM, V17, P49, DOI 10.1002/(SICI)1096-987X(19960115)17:1<49::AID-JCC5>3.0.CO
  • [16] 2-0
  • [17] Peptide and the origin of life
    Rode, BM
    [J]. PEPTIDES, 1999, 20 (06) : 773 - 786
  • [18] Bi- and tricyclic penta- and hexacoordinated phosphoranes with varying ring sizes: Synthesis, structures, and reactivity
    Said, MA
    Pulm, M
    HerbstIrmer, R
    Swamy, KCK
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (41) : 9841 - 9849
  • [19] A common intermediate for prebiotic synthesis of proteins and nucleosides:: a density functional theory (DFT) study on the formation of penta-coordinate phosphorus carboxylic-phosphoric mixed anhydride from N-phosphoryl amino acids
    Tan, B
    Lee, MC
    Cui, M
    Liu, T
    Chen, ZZ
    Li, YM
    Ju, Y
    Zhao, YF
    Chen, KX
    Jiang, HL
    [J]. JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2004, 672 (1-3): : 51 - 60
  • [20] SELF-CONSISTENT REACTION FIELD-THEORY OF SOLVENT EFFECTS
    TAPIA, O
    GOSCINSKI, O
    [J]. MOLECULAR PHYSICS, 1975, 29 (06) : 1653 - 1661
123