Photochemical Steps in the Prebiotic Synthesis of Purine Precursors from HCN

被引：34

作者：

Boulanger, Eliot ^{[1
]}

Anoop, Anakuthil ^{[2
]}

Nachtigallova, Dana ^{[3
]}

Thiel, Walter ^{[1
]}

Barbatti, Mario ^{[1
]}

机构：

[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany

[2] Indian Inst Technol, Dept Chem, Kharagpur 721302, W Bengal, India

[3] AS CR, Inst Organ Chem & Biochem, Prague 16610 6, Czech Republic

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 31期

关键词：

computational chemistry; hydrogen cyanide chemistry; photochemistry; prebiotic synthesis; simulations; HYDROGEN-CYANIDE; CHEMICAL EVOLUTION; CONVERSION; DIAMINOMALEONITRILE; DIAMINOFUMARONITRILE; ENAMINONITRILES; ADENINE; 4-AMINO-5-CYANOIMIDAZOLE; IMIDAZOLES; CHEMISTRY;

D O I：

10.1002/anie.201303246

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

So much excitement: The mechanism for the photoconversion of the HCN tetramer into a precursor of purine nucleobases and nucleotides has been revealed by computational methods. Dissipation of the photoenergy in less than 2 ps eliminates the possibility of hot-ground-state reactions. Instead, a series of photoexcitations followed by internal conversion (IC) drives the reaction via an excited azetene (see picture). Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：8000 / 8003

页数：4

共 29 条

[1] The chemistry of diaminomaleonitrile and its utility in heterocyclic synthesis [J].

Al-Azmi, A ;

Elassar, AZA ;

Booth, BL .

TETRAHEDRON, 2003, 59 (16) :2749-2763

[2] Statistical Rice-Ramsperger-Kassel-Marcus quasiequilibrium theory calculations in mass spectrometry [J].

Baer, T ;

Mayer, PM .

JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, 1997, 8 (02) :103-115

[3] Guanine, Adenine, and Hypoxanthine Production in UV-Irradiated Formamide Solutions: Relaxation of the Requirements for Prebiotic Purine Nucleobase Formation [J].

Barks, Hannah L. ;

Buckley, Ragan ;

Grieves, Gregory A. ;

Di Mauro, Ernesto ;

Hud, Nicholas V. ;

Orlando, Thomas M. .

CHEMBIOCHEM, 2010, 11 (09) :1240-1243

[4] SPECTROSCOPIC AND PHOTOCHEMICAL STUDY OF DIAMINOMALEONITRILE AND DIAMINOFUMARONITRILE [J].

BECKER, RS ;

KOLC, J ;

ROTHMAN, W .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (04) :1269-1273

[5] NUMBER OF MULTIPLY-RESTRICTED PARTITIONS [J].

BEYER, T ;

SWINEHART, DF .

COMMUNICATIONS OF THE ACM, 1973, 16 (06) :379-379

[6] PHOTOCHEMICAL CONVERSION OF 1-AMINO-2-CYANOETHYLENE TO IMIDAZOLE - AN ABINITIO SCF-CI STUDY [J].

BIGOT, B ;

ROUX, D .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (14) :2872-2879

[7] Ultrafast Dynamics of UV-Excited Imidazole [J].

Crespo-Otero, Rachel ;

Barbatti, Mario ;

Yu, Hui ;

Evans, Nicholas L. ;

Ullrich, Susanne .

CHEMPHYSCHEM, 2011, 12 (17) :3365-3375

[8] GAUSSIAN-BASIS SETS FOR USE IN CORRELATED MOLECULAR CALCULATIONS .1. THE ATOMS BORON THROUGH NEON AND HYDROGEN [J].

DUNNING, TH .

JOURNAL OF CHEMICAL PHYSICS, 1989, 90 (02) :1007-1023

[9] AMINOMALONONITRILE AND 4-AMINO-5-CYANOIMIDAZOLE IN HYDROGEN CYANIDE POLYMERIZATION AND ADENINE SYNTHESIS [J].

FERRIS, JP ;

ORGEL, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (21) :4976-&

[10] CHEMICAL EVOLUTION .3. PHOTOCHEMICAL CONVERSION OF ENAMINONITRILES TO IMIDAZOLES [J].

FERRIS, JP ;

KUDER, JE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (08) :2527-+

← 1 2 3 →