L-Leucinamide hydrogensquarate: Spectroscopic and structural elucidation

Amino Acids

Volumn 37, Issue 4, 2009, Pages 693-701

  Kolev, Tsonko ^a   Zareva, Sonya ^b   Mayer Figge, Heike ^c   Spiteller, Michael ^a   Sheldrick, William S ^c   Koleva, Bojidarka B ^c  

^a TU DORTMUND UNIVERSITY   (Germany)

^b UNIVERSITY OF SOFIA   (Bulgaria)

^c RUHR UNIVERSITY BOCHUM   (Germany)

Author keywords

1H NMR data; Ab initio calculations; Crystal structure; L Leucinamide hydrogensquarate; Solid state IR LD spectroscopy

Indexed keywords

AMINO ACID DERIVATIVE; LEUCINAMIDE HYDROGENSQUARATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; COLLOID; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; HOST; HYDROGEN BOND; INFRARED RADIATION; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN STRUCTURE; SOLID; SPECTROSCOPY; X RAY DIFFRACTION;

CRYSTALLIZATION; CYCLOBUTANES; HYDROGEN BONDING; LEUCINE; MOLECULAR STRUCTURE; X-RAY DIFFRACTION;

EID: 70349590531     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-008-0189-4     Document Type: Article

References (38)

1. Chemla D, Zyss J (eds) (1987) Nonlinear optical properties of organic molecules and crystals, vol 1. Academic Press, New York, pp 23-187
2. 2 at 90 K and the structure-based energy estimations Chem Lett 32 1102 1003 10.1246/cl.2003.1102 1:CAS:528:DC%2BD3sXpslGlt7Y%3D
3. BA Eipper RE Mains 1988 Peptide alpha-amidation Annu Rev Physiol 50 333 344 10.1146/annurev.ph.50.030188.002001 3288096 10.1146/annurev.ph.50.030188. 002001 1:CAS:528:DyaL1cXitFyjsLg%3D
4. H Head-Gordon M Head-Gordon MJ Frisch C Brooks III J Pople 1991 Theoretical study of blocked glycine and alanine peptide analogs J Am Chem Soc 113 5989 5997 10.1021/ja00016a010 10.1021/ja00016a010 1:CAS:528: DyaK3MXkvFaru7k%3D
5. 2 Acta Crystallogr 25B 1824 1833
6. Y In M Fujii Y Sasada Y Ishida 2001 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 comparison with their C-unamidated counterparts Acta Crystallogr B 57 72 81 10.1107/S0108768100013975 11173369 10.1107/S0108768100013975 1:STN:280:DC%2BD3M3hsVGrtQ%3D%3D (Pubitemid 33614298)
7. BB Ivanova MG Arnaudov PR Bontchev 2004 IR/LD analysis of Cu(I) complex of homocysteine Spectrochim Acta 60A 855 1:CAS:528:DC%2BD2cXhsVKgtbs%3D
8. BB Ivanova DL Tsalev MG Arnaudov 2006 Validation of reducing-difference procedure for the interpretation of non-polarized infrared spectra of n-component solid mixtures Talanta 69 822 828 10.1016/j.talanta.2005.11.026 18970643 10.1016/j.talanta.2005.11.026 1:CAS:528:DC%2BD28XltVWitbk%3D (Pubitemid 43729915)
9. BB Ivanova V Simeonov M Arnaudov D Tsalev 2007 Linear-dichroic infrared spectroscopy - validation and experimental design of the orientation technique as suspension in nematic liquid crystal Spectrochim Acta [A] 67A 66 75 10.1016/j.saa.2006.06.025 10.1016/j.saa.2006.06.025 1:CAS:528: DC%2BD2sXjs1Omtbc%3D (Pubitemid 46498933)
10. CU Kim PF Misco 1992 A facile synthesis of 1-Hydroxy-2- phosphonocyclobutenedione Tetrahedron Lett 33 3961 3962 10.1016/0040-4039(92) 88072-D 10.1016/0040-4039(92)88072-D 1:CAS:528:DyaK38XlvFWqsL4%3D
11. T Kolev R Petrova M Spiteller 2004 (R)-2-[(2-Ethoxy-3, 4-dioxocyclobut-1-en-1-yl)amino]-3-phenylpropanamide hemihydrate Acta Crystallogr E 60 o634 10.1107/S1600536804006361 (Pubitemid 40650199)
12. T Kolev M Spiteller WS Sheldrick H Mayer-Figge 2005 1-(Aminocarbonyl) ethylammonium hydrogensquarate monohydrate Acta Crystallogr E 61 o4292 o4293 10.1107/S1600536805038079 (Pubitemid 43296130)
13. T Kolev M Spiteller WS Sheldrick H Mayer-Figge T Van Almsick 2006 l-Tyrosinamide hydrochloride monohydrate Acta Crystallogr E 61 o3819 10.1107/S1600536805033131
14. T Kolev E Cherneva M Spiteller WS Sheldrick H Mayer-Figge 2006 l-Methioninamide ester amide of squaric acid diethyl ester Acta Crystallogr E 62 o1390 o1392 10.1107/S1600536806008440 (Pubitemid 43843628)
15. T Kolev BB Koleva E Cherneva M Spiteller WS Sheldrick H Mayer-Figge 2006 Crystal structure, IR-LD spectroscopic, theoretical and vibrational analysis of valinamide ester amide of squaric acid diethyl ester Struct Chem 17 491 499 10.1007/s11224-006-9071-8 10.1007/s11224-006-9071-8 1:CAS:528:DC%2BD28Xht1OhtrzJ (Pubitemid 44876313)
16. T Kolev D Yancheva M Spiteller WS Sheldrick H Mayer-Figge 2006 l-Prolinamidium hydrogensquarate Acta Crystallogr E62 o463 o464 1:CAS:528:DC%2BD28XhtVaqtbo%3D
17. T Kolev M Spiteller WS Sheldrick H Mayer-Figge 2006 l-Argininamidium bis(hydrogensquarate) Acta Crystallogr C 62 o299 o300 10.1107/S0108270106012108 16679609 10.1107/S0108270106012108 (Pubitemid 43813684)
18. T Kolev BB Koleva M Spiteller 2007 Spectroscopic and theoretical characterization of hydrogensquarates of l-threonyl-l-serine and l-serine prediction of structures of the neutral and protonated forms of the dipeptide Amino Acids 33 719 725 10.1007/s00726-006-0391-1 17665275 10.1007/s00726-006- 0391-1 1:CAS:528:DC%2BD2sXhtlSlsrbI (Pubitemid 350165423)
19. Kolev T, Koleva BB, Seidel RW, Mayer-Figge H, Spiteller M, Sheldrick WS (2007b) Tyrammonium 4-nitrophthalate dihydrate - structural and spectroscopic elucidation. Amino Acids. doi: 10.1007/s00726-007-0021-6
20. Kolev TM, Koleva BB, Spiteller M, Sheldrick WS, Mayer-Figge H (2008a) Synthesis, spectroscopic and structural elucidation of tyrosinamide hydrogensquarate monohydrate. Amino Acids. doi: 10.1007/s00726-008-0047-4
21. Kolev TM, Koleva BB, Spiteller M, Sheldrick WS, Mayer-Figge H (2008b) Synthesis, spectroscopic and structural elucidation of sympathomimetic amine, tyraminium dihydrogenphosphate. Amino Acids. doi: 10.1007/s00726-008-0046-5
22. Koleva BB, Kolev TM, Simeonov V, Spassov T, Spiteller M (2008) Linear polarized IR-spectroscopy of partial oriented solids as a colloid suspension in nematic liquid crystal - new tool for structural elucidation of the chemical compounds. J Inclus Prenome. doi: 10.1007/s10847-008-9425-5
23. R Kulathila KA Merkler DJ Merkler 1999 Enzymatic formation of C-terminal amides Nat Prod Rep 16 145 155 10.1039/a801346b 10331284 10.1039/a801346b 1:CAS:528:DyaK1MXitFajs7s%3D (Pubitemid 29207718)
24. D Merkler 1994 C-Terminal amidated peptides: production by the in vitro enzymatic amidation of glycine-extended peptides and the importance of the amide to bioactivity J Enzyme Microb Technol 16 450 456 10.1016/0141-0229(94)90014-0 10.1016/0141-0229(94)90014-0 1:CAS:528:DyaK2cXktlKisLg%3D
25. Michl J, Thulstrup E (1986) Spectroscopy with polarized light. Solute alignment by photoselection, in liquid crystals, polymers, and membranes. VCH Publishers, New York
26. Nalwa HS, Watanabe T, Miyata S (1997) In: Nalwa HS, Miyata S (eds) Nonlinear optics of organic molecules and polymers. CRC Press, Boca Raton, pp 89-29
27. Gaussian 98: Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery Jr JA, Stratmann R, Burant C, Dapprich S, Millam M, Daniels A, Kudin K, Strain M, Farkas P, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Salvador P, Dannenberg JJ, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komáromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JP. Gaussian 98. Gaussian, Inc., Pittsburgh, 1998
28. R Puliti CA Mattia C Giancola G Barone 2001 Crystal structure and conformational stability of N-acetyl-l-prolyl-l-leucinamide. Comparison between structural and thermophysical data J Mol Struct 553 117 130 10.1016/S0022- 2860(00)00537-8 10.1016/S0022-2860(00)00537-8
29. G Ramachandran V Sasisekharan 1968 Conformation of polypeptides and proteins Adv Protein Chem (Kyoto) 23 283 437 10.1016/S0065-3233(08)60402-7 1:CAS:528:DyaE3cXhtFOmsL8%3D
30. Sheldrick GM (1997a) SHELXS-97. Program for crystal structure solution. University of Cottingen, Germany
31. Sheldrick GM (1997b) SHELXL-97. Program for crystal structure solution. University of Cottingen, Germany
32. S Suwan M Isobe O Yamashita H Minakata K Imai 1994 Silkworm diapause hormone, structure-activity relationships indispensable role of C-terminal amide Ins Biochem Mol Biol 24 1001 1007 1:CAS:528:DyaK2MXjt1Oru7o%3D
33. F Sztaricskai A Sum E Roth I Pelyvas S Sandor G Batta P Herczegh P Remenyi Z Miklan F Hudecz 2005 A new class of semisynthetic anthracycline glycoside antibiotics incorporating a squaric acid moiety J Antibiot 58 704 714 16466024 10.1038/ja.2005.96 1:CAS:528:DC%2BD2MXhtlWnu7bJ
34. A Tevyashova F Sztaricskai G Batta P Herczegh A Jeney 2004 Formation of squaric acid amides of anthracycline antibiotics synthesis and cytotoxic properties Bioorg Med Chem Lett 14 4783 4789 10.1016/j.bmcl.2004.06.072 15324908 10.1016/j.bmcl.2004.06.072 1:CAS:528:DC%2BD2cXmvV2htb4%3D (Pubitemid 39490309)
35. R Vargas J Garza B Hay D Dixon 2002 Conformational study of the alanine dipeptide at the MP2 and DFT levels J Phys Chem A 106 3213 3218 10.1021/jp013952f 10.1021/jp013952f 1:CAS:528:DC%2BD38XhslGhtbw%3D (Pubitemid 35264133)
36. JJ Wolff R Wortmann 1999 For a general introduction to non-linear optics of organic compounds Adv Phys Org Chem 32 121 152 10.1016/S0065-3160(08)60007-6 10.1016/S0065-3160(08)60007-6 1:CAS:528:DyaK1MXlsFGktr0%3D
37. J Xie AB Comeau CT Seto 2004 Squaric Acids: a new motif for designing inhibitors of protein tyrosine phosphatases Org Lett 6 83 86 10.1021/ol036121w 14703356 10.1021/ol036121w 1:CAS:528:DC%2BD3sXps1Gltrg%3D (Pubitemid 38160995)
38. S Zimmerman M Pottle G Nemethy H Scheraga 1977 Conformational analysis of the 20 naturally occurring amino acid residues using ECEPP Macromolecules 10 1 9 839855 10.1021/ma60055a001 1:CAS:528:DyaE2sXktVKgs7s%3D