Literature DB >> 23690241

Deracemization of amino acids by partial sublimation and via homochiral self-organization.

Arkadii V Tarasevych1, Alexander E Sorochinsky, Valery P Kukhar, Jean-Claude Guillemin.   

Abstract

Deracemization of a 50/50 mixture of enantiomers of aliphatic amino acids (Ala, Leu, Pro, Val) can be achieved by a simple sublimation of a pre-solubilized solid mixture of the racemates with a huge amount of a less-volatile optically active amino acid (Asn, Asp, Glu, Ser, Thr). The choice of chirality correlates with the handedness of the enantiopure amino acids--Asn, Asp, Glu, Ser, and Thr. The deracemization, enantioenrichment and enantiodepletion observed in these experiments clearly demonstrate the preferential homochiral interactions and a tendency of natural amino acids to homochiral self-organization. These data may contribute toward an ultimate understanding of the pathways by which prebiological homochirality might have emerged.

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Year:  2013        PMID: 23690241     DOI: 10.1007/s11084-013-9333-6

Source DB:  PubMed          Journal:  Orig Life Evol Biosph        ISSN: 0169-6149            Impact factor:   1.950


  21 in total

1.  Enantioenrichment in sublimed amino acid mixtures.

Authors:  Cristóbal Viedma; José E Ortiz; Trinidad de Torres; Pedro Cintas
Journal:  Chem Commun (Camb)       Date:  2012-03-02       Impact factor: 6.222

2.  The origin of biological homochirality.

Authors:  Donna G Blackmond
Journal:  Philos Trans R Soc Lond B Biol Sci       Date:  2011-10-27       Impact factor: 6.237

3.  Thermodynamic control of asymmetric amplification in amino acid catalysis.

Authors:  Martin Klussmann; Hiroshi Iwamura; Suju P Mathew; David H Wells; Urvish Pandya; Alan Armstrong; Donna G Blackmond
Journal:  Nature       Date:  2006-06-01       Impact factor: 49.962

4.  An astrophysically-relevant mechanism for amino acid enantiomer enrichment.

Authors:  Stephen P Fletcher; Richard B C Jagt; Ben L Feringa
Journal:  Chem Commun (Camb)       Date:  2007-04-27       Impact factor: 6.222

5.  Thermal formation of homochiral serine clusters and implications for the origin of homochirality.

Authors:  Pengxiang Yang; Ruifeng Xu; Sergio C Nanita; R Graham Cooks
Journal:  J Am Chem Soc       Date:  2006-12-27       Impact factor: 15.419

Review 6.  Crystalline architectures as templates of relevance to the origins of homochirality.

Authors:  Isabelle Weissbuch; Meir Lahav
Journal:  Chem Rev       Date:  2011-03-07       Impact factor: 60.622

7.  A laboratory model of a prebiotic, spontaneous, and continuous enantiomeric enrichment process.

Authors:  Stanley I Goldberg
Journal:  Orig Life Evol Biosph       Date:  2013-01-24       Impact factor: 1.950

8.  Serine sublimes with spontaneous chiral amplification.

Authors:  Richard H Perry; Chunping Wu; Marcela Nefliu; R Graham Cooks
Journal:  Chem Commun (Camb)       Date:  2006-12-20       Impact factor: 6.222

9.  Enantiomeric crystallization from DL-aspartic and DL-glutamic acids: implications for biomolecular chirality in the origin of life.

Authors:  C Viedma
Journal:  Orig Life Evol Biosph       Date:  2001-12       Impact factor: 1.950

10.  Racemic D,L-asparagine causes enantiomeric excess of other coexisting racemic D,L-amino acids during recrystallization: a hypothesis accounting for the origin of L-amino acids in the biosphere.

Authors:  Shosuke Kojo; Hiromi Uchino; Mayu Yoshimura; Kyoko Tanaka
Journal:  Chem Commun (Camb)       Date:  2004-09-07       Impact factor: 6.222

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  2 in total

1.  Self-disproportionation of enantiomers of thalidomide and its fluorinated analogue via gravity-driven achiral chromatography: mechanistic rationale and implications.

Authors:  Mayaka Maeno; Etsuko Tokunaga; Takeshi Yamamoto; Toshiya Suzuki; Yoshiyuki Ogino; Emi Ito; Motoo Shiro; Toru Asahi; Norio Shibata
Journal:  Chem Sci       Date:  2014-10-30       Impact factor: 9.825

2.  General approach to the synthesis of the chlorosulfolipids danicalipin A, mytilipin A, and malhamensilipin A in enantioenriched form.

Authors:  Won-jin Chung; Joseph S Carlson; Christopher D Vanderwal
Journal:  J Org Chem       Date:  2014-02-13       Impact factor: 4.354

  2 in total

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