Literature DB >> 24454253

Isovaline monohydrate.

Ray J Butcher1, Greg Brewer2, Aaron S Burton3, Jason P Dworkin4.   

Abstract

The title compound, C5H11NO2·H2O, is an isomer of the α-amino acid valine that crystallizes from water in its zwitterion form as a monohydrate. It is not one of the 20 proteinogenic amino acids that are used in living systems and differs from the natural amino acids in that it has no α-H atom. The compound exhibits hydrogen bonding between the water mol-ecule and the carboxyl-ate O atoms and an amine H atom. In addition, there are inter-molecular hydrogen-bonding inter-actions between the carboxyl-ate O atoms and amine H atoms. In the crystal, these extensive N-H⋯O and O-H⋯O hydrogen bonds lead to the formation of a three-dimensional network.

Entities:  

Year:  2013        PMID: 24454253      PMCID: PMC3885077          DOI: 10.1107/S1600536813031620

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


  7 in total

Review 1.  Understanding prebiotic chemistry through the analysis of extraterrestrial amino acids and nucleobases in meteorites.

Authors:  Aaron S Burton; Jennifer C Stern; Jamie E Elsila; Daniel P Glavin; Jason P Dworkin
Journal:  Chem Soc Rev       Date:  2012-06-15       Impact factor: 54.564

2.  Spoilt for choice: assessing phase behavior models for the evolution of homochirality.

Authors:  Donna G Blackmond; Martin Klussmann
Journal:  Chem Commun (Camb)       Date:  2007-09-17       Impact factor: 6.222

3.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

4.  Evolution of solid phase homochirality for a proteinogenic amino acid.

Authors:  Cristobal Viedma; José E Ortiz; Trinidad de Torres; Toshiko Izumi; Donna G Blackmond
Journal:  J Am Chem Soc       Date:  2008-10-28       Impact factor: 15.419

5.  Enantiomeric excesses in the Murchison meteorite and the origin of homochirality in terrestrial biology.

Authors:  Jeffrey L Bada
Journal:  Proc Natl Acad Sci U S A       Date:  2009-07-30       Impact factor: 11.205

6.  Syntheses and properties of zinc and calcium complexes of valinate and isovalinate: metal alpha-amino acidates as possible constituents of the early Earth's chemical inventory.

Authors:  H Strasdeit; I Büsching; S Behrends; W Saak; W Barklage
Journal:  Chemistry       Date:  2001-03-02       Impact factor: 5.236

7.  Enrichment of the amino acid L-isovaline by aqueous alteration on CI and CM meteorite parent bodies.

Authors:  Daniel P Glavin; Jason P Dworkin
Journal:  Proc Natl Acad Sci U S A       Date:  2009-03-16       Impact factor: 11.205

  7 in total
  3 in total

1.  1-Aza-niumyl-cyclo-butane-1-carboxyl-ate monohydrate.

Authors:  Ray J Butcher; Greg Brewer; Aaron S Burton; Jason P Dworkin
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-01-29

2.  2-Methyl-aspartic acid monohydrate.

Authors:  Greg Brewer; Aaron S Burton; Jason P Dworkin; Ray J Butcher
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-11-30

Review 3.  Insights into Abiotically-Generated Amino Acid Enantiomeric Excesses Found in Meteorites.

Authors:  Aaron S Burton; Eve L Berger
Journal:  Life (Basel)       Date:  2018-05-12
  3 in total

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