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2006 | 4 | 4 | 695-707
Tytuł artykułu

Solid-state linear-dichroic infrared (IR-LD) spectroscopic and theoretical characterization of 2-[(2-ethoxy-3,4-dioxocyclobut-1-en-yl)amino]propanamide

Autorzy
Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
2-[(2-Ethoxy-3,4-dioxocyclobut-1-en-yl)amino]propanamide (N-alaninamidoamide of squaric acid ethyl ester) has been characterized structurally and spectroscopically by ab initio calculations and IR-LD spectroscopy of oriented crystals suspended in a nematic liquid crystal. The results are compared with single crystal X-ray structures illustrating the possibilities of this experimental approach to obtaining structural information as well as assigning IR bands.
Wydawca
Czasopismo
Rocznik
Tom
4
Numer
4
Strony
695-707
Opis fizyczny
Daty
wydano
2006-12-01
online
2006-12-01
Twórcy
autor
  • Faculty of Chemistry, Department of Analytical Chemistry, Sofia University “St. Kl. Ohridsky”, 1164, Sofia, Bulgaria , S.Zarewa@abv.bg
Bibliografia
  • [1] D. Chemla and J. Zyss: Nonlinear Optical Properties of Organic Molecules and Crystals, Vol. 1, D. Chemla, J. Zyss (Eds.), Academic Press, New York, 1988, pp. 23–187.
  • [2] H.S. Nalwa, T. Watanabe and S. Miyata: Nonlinear Optics of Organic Molecules and Polymers, H.S. Nalwa, S. Miyata (Eds.), CRC Press, Boca Raton, 1997, pp. 89–329.
  • [3] T. Kolev, R. Petrova and M. Spiteller: “(R)-2-[(2-Ethoxy-3,4-dioxocyclobut-1-en-1-yl)-amino]-3 phenylpropanamide hemihydrate”, Acta Cryst., Vol. 60E, (2004), pp. o634–o636.
  • [4] T. Kolev, J. Benet-Buchholz and M. Spiteller: “Crystal structure of alaninamide ester amide of squaric acid”, Acta Crystallogr., (2006) submitted.
  • [5] T. Kolev, J. Benet-Buchholz and M. Spiteller: “Crystal structure of prolinamide ester amide of squaric acid”, Acta Crystallogr., (2006) submitted.
  • [6] T. Kolev, J. Benet-Buchholz and M. Spiteller: “Crystal structure of tryptophanamide ester amide of squaric acid”, Acta Crystallogr., (2006) submitted.
  • [7] T. Kolev, E. Cherneva, M. Spiteller, W.S. Sheldrick and H. Mayer-Figge: “L-Methioninamide ester amide of diethylsquaric acid”, Acta Crystallogr., Vol. E62, (2006), pp. o1390–o1392.
  • [8] T. Kolev, B.B. Koleva, E. Cherneva, M. Spiteller, W.S. Sheldrick and H. Mayer-Figge: “Crystal structure, IR-LD spectroscopic, theoretical and vibrational analysis of valinamide ester amide of squaric acid”, Struct. Chem., (2006) in press.
  • [9] T. Kolev, D. Yancheva, M. Spiteller, W.S. Sheldrick and H. Mayer-Figge: “L-Prolinamidium hydrogensquarate”, Acta Cryst. Vol. E62, (2006), pp. o463–o465.
  • [10] T. Kolev, M. Spiteller, W.S. Sheldrick and H. Mayer-Figge: “1-(Aminocarbonyl)ethylammonium hydrogensquarate monohydrate”, Acta Cryst., Vol. E61, (2006), pp. o4292–o4294.
  • [11] T. Kolev, M. Spiteller, W.S. Sheldrick, H. Mayer-Figge and T. van Almsick: “L-Tyrosinamide hydrochloride monohydrate”, Acta Cryst., Vol. E61, (2006), pp. o3819–o3821.
  • [12] T. Kolev, M. Spiteller, W.S. Sheldrick and H. Mayer-Figge: “L-Arginineamide bis(hydrodensquarate)”, Acta Cryst., E, (2006), in press.
  • [13] Y. In, M. Fujii, Y. Sasada and T. Ishida: “Structural studies on C-amidated amino acids and peptides: Structures of hydrochloride salts of C-amidated Ile, Val, Thr, Ser, Met, Trp, Gln and Arg and corresponding C-unamidated counterparts”, Acta. Cryst., Vol. B57, (2001), pp. 72–81.
  • [14] B.A. Eipper and R.E. Mains: “Peptide alpha-amidation”, Ann. Rev. Physiol., Vol. 50, (1988), pp. 333–344. http://dx.doi.org/10.1146/annurev.ph.50.030188.002001[Crossref]
  • [15] R. Kulathila, K.A. Merkler and D.J. Merkler: “Enzymatic formation of C-terminal amides”, Nat. Prod. Rep., Vol. 16, (1999), pp. 145–148. http://dx.doi.org/10.1039/a801346b[Crossref]
  • [16] D. Merkler: “C-terminal amidated peptides: Production by the in vitro enzymatic amidation of glycine extended peptides and the importance of the amides for bioactivity”, J. Enzymme Microb. Technol., Vol. 16, (1994), pp. 450–458. http://dx.doi.org/10.1016/0141-0229(94)90014-0[Crossref]
  • [17] S. Suwan, M. Isobe, O. Yamashita, H. Minakata and K. Imai: “Silkworm diapause hormones - activity relationships indispensable role of C-terminal amides”, Insect Biochem. Mol. Biol., Vol. 24, (1994), pp. 1001–1007. http://dx.doi.org/10.1016/0965-1748(94)90137-6[Crossref]
  • [18] X. Xie, A.B. Comeau and C.T. Seto: “Squaric acid derivatives: A new class of protein tyrosine phosphatase inhibitors”, Org. Lett., Vol. 6, (2004), pp. 83–86. http://dx.doi.org/10.1021/ol036121w[Crossref]
  • [19] J.R. Porter, S.C. Archibald, K. Child, D. Critchley, J.C. Head, J.M. Linsley, T.A.H. Parton, M.K. Robinson, A. Shock, R.J. Taylor, G.J. Warrelow, R.P. Alexander and B. Langhman: “Squaric acid derivatives as VLA-4 integrin antagonists”, Bioorg. Med. Chem. Lett., Vol. 12, (2002), pp. 1051–1054. http://dx.doi.org/10.1016/S0960-894X(02)00075-6
  • [20] M. Burak, A.B. Comeau and C.T. Seto: “Squaric acid-based peptidic inhibitors of matrix metalloprotease-1”, J. Org. Chem., Vol. 70, (2005), pp. 10792–10802. http://dx.doi.org/10.1021/jo0517848[Crossref]
  • [21] A.M. Gilbert, M.M. Antane, T. Argentieri, J.A. Butera, G.D. Francisco, C. Freeden, E.G. Gundersen, R. Graceffa, D. Herbst, B. Hirth, J. Lebbox, C. McFarlane, N. Wesley, D. Quagliato, J. Sheldon, D. Warga, A. Wojdan and M. Woods: “Design and SAR of Novel Potassium Channel openers targeted for urge urinary incontinance. 2. Selective and potent benzylamino cyclobutenediones”, J. Med. Chem., Vol. 43, (2000), pp. 1203–1214. http://dx.doi.org/10.1021/jm9905108[Crossref]
  • [22] B.B. Ivanova, M.G. Arnaudov and P.R. Bontchev: “Linear-dichroic infrared spectral analysis of Cu(I)-homocysteine complex”, Spectrochim. Acta, Part A, Vol. 60(4), (2004), pp. 855–862. http://dx.doi.org/10.1016/S1386-1425(03)00310-X[Crossref]
  • [23] T. Kolev, B.B. Koleva, M. Emgenbroich, M. Spiteller, W.S. Sheldrick and H. Mayer-Figge: “Crystal structure and linear-dichroic infrared (IR-LD) spectral analysis of N,N′-diethyl-4-vinylbenzamidinium squarate”, Struct. Chem., (2006), in press.
  • [24] B.B. Ivanova: “Solid state linear-dichroic infrared (IR-LD) spectral characterization of α-and β-polymorphs of glycine”, Centrl. Europ. J. Chem., Vol. 4, (2006), pp. 111–117. http://dx.doi.org/10.1007/s11532-005-0008-7[Crossref]
  • [25] B.B. Ivanova, M.G. Arnaudov and St.T. Todorov: “Linear-dichroic infrared and NMR spectral analysis of Au3+-complex with the tripeptide glycyl-methionyl-glycine,” J. Coord. Chem., (2005) in press.
  • [26] B.B. Ivanova: “Stereo-structural and IR-spectral characterization of histidine containing dipeptides by means of solid state IR-LD spectroscopy and ab initio calculations”, J. Mol. Struct., Vol. 782, (2006), pp. 122–129. http://dx.doi.org/10.1016/j.molstruc.2005.08.004[Crossref]
  • [27] B.B. Ivanova and M.G. Arnaudov: “Solid state linear-dichroic infrared spectral and theoretical analysis of methionine containing tripeptides”, Spectrochim. Acta, Part A, (2005), in press.
  • [28] B.B. Ivanova, M.G. Arnaudov, St. Todorov, W.S. Sheldrick and H. Mayer-Figge: “Structural analysis of the tripeptide glycyl-methionyl-glycine (H-Gly-Met-Gly-OH) and its hydrochloride”, Struct. Chem., (2005), in press.
  • [29] B.B. Ivanova: “IR-LD spectroscopic characterization of L-Tryptophan containing dipeptides”, Spectrochim. Acta, Part A, (2005) in press.
  • [30] B.B. Ivanova, D.L. Tsalev and M.G. Arnaudov: “Validation of reducing-difference procedure for the interpretation of non-polarized infrared spectra of n-component solid mixtures”, Talanta, Vol. 69, (2006), pp. 822–828. http://dx.doi.org/10.1016/j.talanta.2005.11.026[Crossref]
  • [31] B.B. Ivanova, V.D. Simeonov, M.G. Arnaudov and D.L. Tsalev: “Linear-dichroic infrared spectroscopy - validation and experimental design of the orientation technique as suspension in nematic liquid crystal”, Spectrochim Acta Part A, (2006), submitted. [WoS]
  • [32] DALTON, a molecular electronic structure program, Release 2.0 (2005), http://www.kjemi.uio.no/software/dalton/dalton.html
  • [33] M.G. Arnaudov, B.B. Ivanova and Sh.G. Dinkov: “A linear dichroic infrared (IR-LD) solid state spectral study of 4-aminopyridine”, Vibrational Spectrosc., Vol. 37(1), (2005), pp. 145–147. http://dx.doi.org/10.1016/j.vibspec.2004.08.003
  • [34] N. Roeges: Guide to the complete interpretation of infrared spectra of organic structures, Wiley, New York, 1993, pp. 1–337.
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_s11532-006-0034-0
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