L-amino acids catalyze the formation of an excess of D-glyceraldehyde, and thus of other D sugars, under credible prebiotic conditions

被引:93
作者
Breslow, Ronald [1 ]
Cheng, Zhan-Ling [1 ]
机构
[1] Columbia Univ, Dept Chem, New York, NY 10027 USA
基金
美国国家科学基金会;
关键词
aldol reaction; formaldehyde; formose reaction; meteorites; AMPLIFICATION; ORIGIN;
D O I
10.1073/pnas.1001639107
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
Previous work by us, and others, has shown that the formation of amino acids on prebiotic earth with the geometric arrangement called the L configuration can be understood. Some meteorites of the carbonaceous chondritic type deliver unusual amino acids, with alpha-methyl groups, which have an excess of the L isomers. We previously showed that in decarboxylative transamination reactions under credible prebiotic conditions they produce normal amino acids that also have a preference for the L isomer, as is found in our proteins. We, and others, showed that as little as a 1% excess of the L isomers could be amplified up to a 95/5 ratio of L over D on simple evaporation of a solution, so life could start with such a solution in which the dominant L isomers would be selectively chosen. We now find that the geometry of sugars referred to D, as in D-ribose or D-glucose, is not an independent mystery. D-glyceraldehyde, the simplest sugar with a D center, is the basic unit on which other sugars are built. We find that the synthesis of glyceraldehyde by reaction of formaldehyde with glycolaldehyde is catalyzed under prebiotic conditions to D/L ratios greater than 1, to as much as 60/40, by a representative group of L-amino acids (with the exception of L-proline). The D/L glyceraldehyde ratio in water solution is amplified to 92/8 using simple selective solubilities of the D and the DL forms. This D center would then be carried into the prebiotic syntheses of larger sugars.
引用
收藏
页码:5723 / 5725
页数:3
相关论文
共 15 条
[1]  
[Anonymous], 1959, Tetrahedron Letters
[2]   Amplification of enantiomeric concentrations under credible prebiotic conditions [J].
Breslow, Ronald ;
Levine, Mindy S. .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2006, 103 (35) :12979-12980
[3]   Imitating Prebiotic Homochirality on Earth [J].
Breslow, Ronald ;
Levine, Mindy ;
Cheng, Zhan-Ling .
ORIGINS OF LIFE AND EVOLUTION OF BIOSPHERES, 2010, 40 (01) :11-26
[4]   On the origin of terrestrial homochirality for nucleosides and amino acids [J].
Breslow, Ronald ;
Cheng, Zhan-Ling .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2009, 106 (23) :9144-9146
[5]   Enantiomeric excesses in meteoritic amino acids [J].
Cronin, JR ;
Pizzarello, S .
SCIENCE, 1997, 275 (5302) :951-955
[6]   ASYMMETRIC PHOTOLYSIS OF (RS)-LEUCINE WITH CIRCULARLY POLARIZED UV LIGHT [J].
FLORES, JJ ;
BONNER, WA ;
MASSEY, GA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (11) :3622-3625
[7]   Large nonlinear effect observed in the enantiomeric excess of proline in solution and that in the solid state [J].
Hayashi, Yujiro ;
Matsuzawa, Masayoshi ;
Yamaguchi, Junichiro ;
Yonehara, Sayaka ;
Matsumoto, Yasunobu ;
Shoji, Mitsuru ;
Hashizume, Daisuke ;
Koshino, Hiroyuki .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (28) :4593-4597
[8]   Thermodynamic control of asymmetric amplification in amino acid catalysis [J].
Klussmann, Martin ;
Iwamura, Hiroshi ;
Mathew, Suju P. ;
Wells, David H., Jr. ;
Pandya, Urvish ;
Armstrong, Alan ;
Blackmond, Donna G. .
NATURE, 2006, 441 (7093) :621-623
[9]   Enantiosective synthesis and enantiomeric amplication of amino acids under prebiotic conditions [J].
Levine, Mindy ;
Kenesky, Craig Scott ;
Mazori, Daniel ;
Breslow, Ronald .
ORGANIC LETTERS, 2008, 10 (12) :2433-2436
[10]   A MECHANISM FOR AMPLIFICATION OF FLUCTUATIONS IN RACEMIC MIXTURES [J].
MOROWITZ, HJ .
JOURNAL OF THEORETICAL BIOLOGY, 1969, 25 (03) :491-&