Solid phase synthesis of peptides containing novel amino acids, substituted 3-benzimidazolealanines

Amino Acids

Volumn 36, Issue 2, 2009, Pages 309-315

  Koprowska Ratajska, Małgorzata ^a   Kluczyk, Alicja ^a   Stefanowicz, Piotr ^a   Bartosz Bechowski, Hubert ^a   Szewczuk, Zbigniew ^a  

^a UNIVERSITY OF WROC AW   (Poland)

Author keywords

4 Amino 3 nitrophenylalanine; Benzimidazoles; Combinatorial synthesis; Solid phase peptide synthesis; Unnatural amino acids

Indexed keywords

(4 AMINO 3 NITROPHENYL)ALANINE; 2' (1,3 BENZODIOXOL 5 YL) 3 (1H BENZIMIDAZOL 5 YL)ALANYLGLYCINE; 2' (4 BROMOPHENYL) 3 (1H BENZIMIDAZOL 5 YL)ALANYLGLYCINE; 2' (4 CHLOROPHENYL) 3 (1H BENZIMIDAZOL 5 YL)ALANYLGLYCINE; 2' (PYRIDIN 2 YL) 3 (1H BENZIMIDAZOL 5 YL)ALANYLGLYCINE; 2' (PYRIDIN 4 YL) 3 (1H BENZIMIDAZOL 5 YL)ALANYLGLYCINE; 2' ETHYL 3 (1H BENZIMIDAZOL 5 YL)ALANYLGLYCINE; 2' PHENYL 3 (1H BENZIMIDAZOL 5 YL)ALANYLGLYCINE; 2' PROPYL 3 (1H BENZIMIDAZOL 5 YL)ALANYLGLYCINE; ALANINE DERIVATIVE; ALDEHYDE DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; BETA (3,4 DIAMINOPHENYL)ALANINE; DIPEPTIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; SOLID PHASE SYNTHESIS; SUBSTITUTION REACTION;

ALANINE; BISBENZIMIDAZOLE; PEPTIDES;

EID: 59449105828     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-008-0070-5     Document Type: Article

References (25)

1. M Alamgir DSC Black N Kumar 2007 Synthesis, reactivity and biological activity of benzimidazoles Top Heterocycl Chem 9 87 118
2. Atherton E, Scheppart RC (1989) Solid phase peptide synthesis. IRL Press, Oxford
3. PM Bendale CM Sun 2002 Rapid microwave-assisted liquid-phase combinatorial synthesis of 2-(arylamino)benzimidazoles J Comb Chem 4 359 361
4. N Bendsoe G Ronquist 2004 Inhibition of the l-dopa transport system in human epidermal Langerhans cells by omeprazole and its analogues Amino Acids 26 19 26
5. M Devereux D O'Shea A Kellett M McCann M Walsh D Egan C Deegan K Kedziora G Rosair H Muller-Bunz 2007 Synthesis, X-ray crystal structures and biomimetic and anticancer activities of novel copper(II)benzoate complexes incorporating 2-(4′-thiazolyl)benzimidazole (thiabendazole), 2-(2-pyridyl)benzimidazole and 1,10-phenanthroline as chelating nitrogen donor ligands J Inorg Biochem 101 881 892
6. C Frochot B Di Stasio R Vanderesse MJ Belgy M Dodeller F Guillemin ML Viriot M Barberi-Heyo 2007 Interest of RGD-containing linear or cyclic peptide targeted tetraphenylchlorin as novel photosensitizers for selective photodynamic activity Bioorg Chem 35 205 220
7. AC Hines K Parang RA Kohanski SR Hubbard PA Cole 2005 Bisubstrate analog probes for the insulin receptor protein tyrosine kinase: molecular yardsticks for analyzing catalytic mechanism and inhibitor design Bioorg Chem 33 285 297
8. Huang W, Scarborough RM (1999) A new "traceless" solid-phase synthesis strategy: synthesis of a benzimidazole library. Tetrahedron Lett 40:2665-2668
9. Kotha S, Shah VR, Mishra P, Datta A (2007) Design and synthesis of a novel anthracene-based fluorescent probe through the application of the Suzuki-Miyaura cross-coupling reaction. Amino Acids (in press). (doi: 10.1007/s00726-007-0592-2 )
10. LS Lin TJ Lanza LA Castonguay T Kamenecka E McCauley G Van Riper LA Egger RA Mumford X Tong M MacCoss JA Schmidt WK Halmann 2004 Bioisosteric replacement of anilide with benzoxazole: potent and orally bioavailable antagonists of VLA-4 Bioorg Med Chem Lett 14 2331 2334
11. G Lucchese A Stufano B Trost A Kusalik D Kanduc 2006 Peptidology: short amino acid modules in cell biology and immunology Amino Acids 33 703 707
12. JP Mayer GS Lewis C McGee D Bankaitis-Davis 1998 Solid-phase synthesis of benzimidazoles Tetrahedron Lett 39 6655 6658
13. ME McGrath PA Sprengeler B Hirschbein JR Somoza I Lehoux JW Janc E Gjerstad M Graupe A Estiarte C Venkataramani Y Liu R Yee JD Ho MJ Green CS Lee L Liu V Tai J Spencer D Sperandio BA Katz 2006 Structure-guided design of peptide-based tryptase inhibitors Biochemistry 45 5964 5973
14. JD Milkowski FM Miller EM Johnson Jr N Zenker 1970 Benzimidazole-5(6)- alanine and related compounds. 1. Synthesis of amino acids as inhibitors of norepinephrine biosynthesis J Med Chem 13 741 742
15. A Staszewska P Stefanowicz Z Szewczuk 2005 Direct solid-phase synthesis of quinoxaline-containing peptides Tetrahedron Lett 46 5525 5528
16. P Stefanowicz PJ Boratyński A Staszewska IZ Siemion M Zimecki Z Szewczuk 2004 Threonine at position 6 is not essential for the immunosuppressive activity of HLA-DQ(beta164-172)-hexapeptide Mol Immunol 41 911 917
17. P Stefanowicz L Jaremko M Jaremko A Staszewska Z Szewczuk I Bryndal T Lis 2006 (2S)-3-(4-Amino-3-nitrophenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino) propanoic acid dichloromethane disolvate Acta Cryst E62 o3555 o3557
18. P Stefanowicz K Kapczynska A Kluczyk Z Szewczuk 2007 A new procedure for the synthesis of peptide-derived Amadori products on a solid support Tetrahedron Lett 48 967 969
19. Stefanowicz P, Staszewska A, Kluczyk A, Zimecki M, Szewczuk Z (2007b) Immunomodulatory properties and fragmentation pathways of quinoxaline-containing peptides. In: 2nd European conference on chemistry for life sciences, 4-8 September, Wroclaw, Poland, p 299
20. Stone CA (1979) Antihypertensive compositions containing an aryl-substituted alanine azo and an arylhydrazino-propionic acid. U.S. Patent 4,156,734; Chem Abstr 91:211822
21. 2+ ions are effective DNA cleaving agents. In: 2nd European conference on chemistry for life sciences, 4-8 September, Wroclaw, Poland, p 304
22. Z Szewczuk P Stefanowicz A Wilczyński IZ Siemion CS Cierniewski U Kralisz Z Wieczorek 1996 The immunosuppressory and adhesive miniregion of the human major histocompatibility protein, human leukocyte antigen DQ Biopolymers 40 571 583
23. Z Szewczuk P Stefanowicz A Wilczyński A Staszewska IZ Siemion M Zimecki Z Wieczorek 2004 Immunosuppressory activity of ubiquitin fragments containing retro-RGD sequence Biopolymers 74 352 362
24. CY Wu CM Sun 2002 Soluble polymer-supported synthesis of 2-(arylamino)benzimidazoles Tetrahedron Lett 43 1529 1533
25. Z Wu P Rea G Wickham 2000 'One-pot' nitro reduction-cyclisation solid phase route to benzimidazoles Tetrahedron Lett 41 9871 9874