Summary.
Hydrogensquarates of dipeptide l-threonyl-l-serine (H-Thr-Ser-OH) and l-serine (HSq × Ser) have been synthesized, isolated and spectroscopic characterized by solid-state linear-polarized IR-spectroscopy, 1H- and 13C-NMR, ESI-MS and HPLC with tandem masspectrometry (MS-MS) methods. The structures of the salts and neutral dipeptide have been predicted theoretically by ab initio calculations. In the case of H-Thr-Ser-OH the theoretical data are supported by IR-LD ones. The hydrogensquarates consist in positive charged dipeptide or amino acid moiety and negative hydrogensquarate anion (HSq) stabilizing by strong intermolecular hydrogen bonds. The data about the l-serine hydrogensquarate are compared with known crystallographic data thus indicating a good correlation between the theoretical predicted structures and experimentally obtained by single crystal X-ray diffraction.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
D Chemla J Zyss (1987) Nonlinear optical properties of organic molecules and crystals NumberInSeries1 Academic Press New York 23–187
DALTON (2005) A molecular electronic structure program, Release 2.0 http://www.kjemi.uio.no/software/dalton/dalton.html
AM Gilbert MM Antane TM Argentieri JA Butera GD Francisco C Freeden EG Gundersen RF Graceffa D Herbst BH Hirth JR Lennox G McFarlane NW Norton D Quagliato JH Sheldon D Warga A Wojdan M Woods (2000) ArticleTitleDesign and SAR of novel potassium channel openers targeted for urge urinary incontinence. Selective and potent benzulamino cyclobutenediones J Med Chem 43 1203–1207 Occurrence Handle10737753 Occurrence Handle10.1021/jm9905108 Occurrence Handle1:CAS:528:DC%2BD3cXhsValu7s%3D
Ivanova BB (2006a) Aromatic dipeptides and their salts – solid-state linear-dichroic infrared (IR-LD) spectral analysis and ab initio calculations. Spectrochim Acta Part A (in press)
BB Ivanova (2006b) ArticleTitleStereo-structural and IR-spectral characterization of histidine containing dipeptides by means of solid state IR-LD spectroscopy and ab initio calculations J Mol Struct 782 122–129 Occurrence Handle10.1016/j.molstruc.2005.08.004 Occurrence Handle1:CAS:528:DC%2BD28XptVamtw%3D%3D
BB Ivanova (2006c) ArticleTitleIR-LD spectroscopic characterization of l-Tryptophan containing dipeptides Spectrochim Acta Part A 64 931–938 Occurrence Handle10.1016/j.saa.2005.08.022
T Kolev R Stahl H Preut P Bleckmann V Radomirska (1998) ArticleTitleCrystal structure of L-(+)-serinium hydrogensquarate, C7H9NO7 Z Krist New Crystal Struct 213 169–170 Occurrence Handle1:CAS:528:DyaK1cXivVSg
T Kolev (2006) ArticleTitleSolid-state IR-LD spectroscopic and theoretical analysis of arginine-containing peptides Biopolymers 83 39–45 Occurrence Handle16628677 Occurrence Handle10.1002/bip.20525 Occurrence Handle1:CAS:528:DC%2BD28XosFCqs74%3D
J Michl EW Thulstrup (1986) Spectroscopy with polarized light SeriesTitleSolute alignment by photo-selection, in liquid crystals, polymers, and membranes VCH Publishers New York
A Moen M Froseth CH Gorbitz B Dalhus (2004) ArticleTitleA non-planar peptide bond in l-seryl-l-valine Acta Crystallogr 60C o564–o565
HS Nalwa T Watanabe S Miyata (1997) Nonlinear optics of organic molecules and polymers CRC Press Boca Raton 89–329
KA Netland K Andresen CH Gorbitz B Dalhus (2004) ArticleTitle l-Alanyl-l-threonine Acta Crystallogr 60E o951–o953
L Nord P Vaag J Duus (2004) ArticleTitleQuantification of organic and amino acids in beer by 1H. NMR Spectroscopy Anal Chem 76 4790–4798 Occurrence Handle15307790 Occurrence Handle10.1021/ac0496852 Occurrence Handle1:CAS:528:DC%2BD2cXltVKru70%3D
MB Onaran AB Comeau CT Seto (2005) ArticleTitleSquaric acid-based peptidic inhibitors of matrix metalloprotease-1 J Org Chem 70 10792–10798 Occurrence Handle16356002 Occurrence Handle10.1021/jo0517848 Occurrence Handle1:CAS:528:DC%2BD2MXht1WltLzE
J Slowikowska J Lipkowski (2001) ArticleTitle l-Seryl-l-leucine Acta Crystallogr 57C 187–189
X Xie AB Comeau CT Seto (2004) ArticleTitleSquaric acid: A new motif for designing inhibitors of protein tyrosine phosphatases Org Lett 6 83–94 Occurrence Handle14703356 Occurrence Handle10.1021/ol036121w Occurrence Handle1:CAS:528:DC%2BD3sXps1Gltrg%3D
VS Yadava VM Padmanabhan (1973) ArticleTitleThe crystal structure of glycyl-l-threonine dihydrate Acta Crystallogr 29C 854–858
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Kolev, T., Koleva, B. & Spiteller, M. Spectroscopic, theoretical and structural characterization of hydrogensquarates of l-threonyl-l-serine and l-serine. Amino Acids 33, 719–725 (2007). https://doi.org/10.1007/s00726-006-0391-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00726-006-0391-1