Received 18 November 2013
aDepartment of Chemistry, Catholic University of America, Washington, DC 20064, USA,bNASA Goddard Space Flight Center, Greenbelt, MD 20771, USA,cSolar System Exploration Division, NASA Goddard Space Flight Center, Greenbelt, MD 20771, USA, and dDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
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The title compound, C5H9NO4·H2O, is an isomer of the -amino acid glutamic acid that crystallizes from water in its zwitterionic 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 an -methyl group rather than an -H atom. In the crystal, an O-HO hydrogen bond is present between the acid and water molecules while extensive N-HO and O-HO hydrogen bonds link the components into a three-dimensional array.
For the eighty amino acids that have been detected in meteorites or comets, see: Pizzarello et al. (2006); Glavin & Dworkin, (2009); Burton et al. (2012). For the role that crystallization plays in chiral separation, see: Blackmond & Klussmann (2007); Blackmond et al. (2008). For the role of the H atom on the -C atom in enhancing the rate of racemization, see: Yamada et al. (1983). For the mechanism of racemization of amino acids lacking an -H atom, see: Pizzarello & Groy (2011). For the role that crystallization can play in the enrichment of L isovaline and its structure, see: Glavin & Dworkin (2009); Butcher et al. (2013). For normal bond lengths and angles, see: Orpen (1993). For the number of -methyl amino acids that have been observed with L-enantiomeric excesses up to 20% that are not believed to be the result of contamination, see: Pizzarello & Cronin (2000); Glavin & Dworkin (2009); Glavin et al. (2011, 2012); Burton et al. (2013).
Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5362 ).
RJB wishes to acknowledge the NSF-MRI program (grant CHE-0619278) for funds to purchase the diffractometer. GB wishes to acknowledge support of this work from NASA (NNX10AK71A).
Agilent (2012). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England.
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