A Unified Mechanism for Abiotic Adenine and Purine Synthesis in Formamide

被引:64
作者
Hudson, Jeremy S. [1 ]
Eberle, Joseph F. [1 ]
Vachhani, Raj H. [1 ]
Rogers, Luther C. [1 ]
Wade, James H. [1 ]
Krishnamurthy, Ramanarayanan [2 ]
Springsteen, Greg [1 ]
机构
[1] Furman Univ, Dept Chem, Greenville, SC 29613 USA
[2] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
关键词
cyanides; formamide; nucleobases; prebiotic chemistry; purines; PRIMITIVE EARTH CONDITIONS; ONE-STEP SYNTHESIS; PREBIOTIC SYNTHESIS; HYDROGEN-CYANIDE; NUCLEIC-ACIDS; NUCLEOBASES; ORIGIN; LIFE; CHEMISTRY; 4-AMINO-5-CYANOIMIDAZOLE;
D O I
10.1002/anie.201108907
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Form(am)idable beginning: Mechanistic pathways from formamide to purine and adenine have been proposed (see scheme, purine (R=H, X=H), adenine (R=CN, X=NH 2, R'=CONH 2). Parallels between these plausible prebiotic syntheses and purine-ring biosynthesis may allude to the origins of the metabolic route. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:5134 / 5137
页数:4
相关论文
共 34 条
[1]   THE SYNTHESIS OF HETEROCYCLES VIA ADDITION ELIMINATION-REACTIONS OF 4-AMINOIMIDAZOLES AND 5-AMINOIMIDAZOLES [J].
ALSHAAR, AHM ;
CHAMBERS, RK ;
GILMOUR, DW ;
LYTHGOE, DJ ;
MCCLENAGHAN, I ;
RAMSDEN, CA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (21) :2789-2811
[2]   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
[3]  
BREDERECK H, 1962, LIEBIGS ANN CHEM, V659, P133
[4]  
Bredereck H., 1956, [No title captured], Patent No. [DE 941289, 941289]
[5]   Carbonaceous meteorites contain a wide range of extraterrestrial nucleobases [J].
Callahan, Michael P. ;
Smith, Karen E. ;
Cleaves, H. James, II ;
Ruzicka, Josef ;
Stern, Jennifer C. ;
Glavin, Daniel P. ;
House, Christopher H. ;
Dworkin, Jason P. .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2011, 108 (34) :13995-13998
[6]   Synthesis of HCN Polymer from Thermal Decomposition of Formamide [J].
Cataldo, Franco ;
Patane, Giacomo ;
Compagnini, Giuseppe .
JOURNAL OF MACROMOLECULAR SCIENCE PART A-PURE AND APPLIED CHEMISTRY, 2009, 46 (11) :1039-1048
[7]   STUDIES IN PREBIOTIC SYNTHESIS .I. AMINOMALONONITRILE AND 4-AMINO-5-CYANOIMIDAZOLE [J].
FERRIS, JP ;
ORGEL, LE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (16) :3829-&
[8]   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-&
[9]   AN UNUSUAL PHOTOCHEMICAL REARRANGEMENT IN SYNTHESIS OF ADENINE FROM HYDROGEN CYANIDE [J].
FERRIS, JP ;
ORGEL, LE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (05) :1074-&
[10]   PREBIOTIC SYNTHESIS OF PURINES FROM METABOLIC INTERMEDIATES [J].
KATSIGIANNIS, C ;
MAR, A ;
ORO, J .
ORIGINS OF LIFE AND EVOLUTION OF THE BIOSPHERE, 1986, 16 (3-4) :297-298