Preferential polymerization of 5-(aminomethyl)-2-furancarboxylic acid (AMFC) into a cyclic tripeptide

Journal of Theoretical and Computational Chemistry

Volumn 3, Issue 4, 2004, Pages 555-566

  Singh, Harjinder ^a   Arora, Karunesh ^b   Tapadar, Subhasish ^c   Chakraborty, Tushar K ^c  

^a PANJAB UNIVERSITY   (India)

^b NEW YORK UNIVERSITY   (United States)

^c INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

5 (aminomethyl) 2 furancarboxylic acid; ab initio; Free energy; Onsager reaction field model

Indexed keywords

5 AMINOMETHYL 2 FURAN CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; DIMER; FURAN; OLIGOPEPTIDE; OXYGEN; SOLVENT; TRIPEPTIDE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; ATOM; CALCULATION; ELECTRICITY; ENERGY; GEOMETRY; PARAMETER; POLYMERIZATION; QUANTUM CHEMISTRY; ROOM TEMPERATURE; THEORETICAL STUDY; THERMODYNAMICS;

EID: 12144259010     PISSN: 02196336     EISSN: None     Source Type: Journal    
DOI: 10.1142/S0219633604001203     Document Type: Article

References (48)

1. (a) Chakraborty TK, Tapadar S, Kumar SK, Tetrahedron Lett 43:1317, 2002.
2. (b) Chakraborty TK, Tapadar S, Raju TV, Annapurna J, Singh H, SYNLETT 2004, in press.
3. (a) Boden CDJ, Norley M, Pattenden G, J Chem Soc Perkin Trans 1 883, 2000.
4. (b) Boden CDJ, Pattenden G, J Chem Soc Perkin Trans 1 875, 2000.
5. (c) Wipf P, Akaloids: Chemical and Biological Perspectives; Pelletier SW, (ed.), Elsevier, Amsterdam, 12:187, 1998.
6. (d) Ogino J, Moore RE, Patterson GML, Smith CD, J Natl Prod 59:581, 1996.
7. (e) Boden CDJ, Pattenden G, Tetrahadron Lett 36:6153, 1995.
8. (f) Degnan BM, Hawkins CJ, Lavin MF, McCaffery EJ, Parry DL, van den Brenk AL, Watters DJ, J Med Chem 32:1349, 1989.
9. (g) Schmitz FJ, Ksebati MB, Chang JS, Wang JL, Hossain MB, van der Helm D, Engel MH, Serban A, Silfer JA, J Org Chem 54:3463, 1989.
10. (h) Hamada Y, Kato S, Shioiri T, Tetrahedron Lett 26:3223, 1985.
11. (i) Hamamoto Y, Endo M, Nakagawa M, Nakanishi T, Mizukawa K, J Chem Soc Chem Commun 323, 1983.
12. (a) Bernhardt PV, Comba, P, Fairlie DP, Gahan LR, Hanson GR, Lötzbeyer L, Chem Eur J 8:1527, 2002.
13. (b) Morris LA, Milne BF, Thompson GS, Jasper M, J Chem Soc Perkin Trans 2:1072, 2002.
14. (c) Cusack RM, Grøndahl L, Fairlie DP, Gahan LR, Hanson GR, J Chem Soc Perkin Trans 2:556, 2002.
15. (d) Morris LA, Milne BF, Jasper M, Kettenes-van den Bosch JJ, Versluis K, Heck AJR, Kelly SM, Price NC, Tetrahedron 57:3199, 2001.
16. (e) Morris LA, Jasper M, Kettenes-van den Bosch JJ, Versluis K, Heck AJR, Kelly SM, Price NC, Tetrahedron 57:3185, 2001.
17. (f) Cusack RM, Grøndahl L, Abbenanate G, Fairlie DP, Gahan LR, Hanson GR, Hambley TW, J Chem Soc Perkin Trans 2:323, 2000.
18. (g) Grøndahl L, Sokolenko N, Abbenanate G, Fairlie DP, Gahan LR, J Chem Soc Dalton Trans 1227, 1999.
19. (h) Freeman DJ, Pattenden G, Drake AF, Siligardi G, J Chem Soc Perkin Trans 2:129, 1998.
20. (i) van den Brenk AL, Fairlie DP, Gahan LR, Hanson GR, Hambley TW, Inorg Chem 35:1095, 1996.
21. (j) van den Brenk AL, Fairlie DP, Gahan LR, Hanson GR, Hawkins CJ, Jones A, Kennard CHL, Moubaraki B, Murray KS, Inorg Chem 33:3549, 1994.
22. (k) Wipf P, Venkatraman S, Miller CP, Geib SJ, Angew Chem Int Ed Engl 33:1516, 1994.
23. (l) Michael JP, Pattenden G, Angew Chem Int Ed Engl 32:1, 1993.
24. Hamilton AD (ed.), Molecular Recognition Tetrahedron Symposia in Print No. 56 [Tetrahedron 51(2), 1995], Pergamon Press, Oxford, UK.
25. Gellman SH (ed.), Molecular Recognition [Chem Rev 97(5), 1997], American Chemical Society; Washington, DC, USA.
26. Perry JJB, Kilburn JD, Contemp Org Syn 4:61, 1997.
27. (a) Jayaprakash S, Pattenden G, Viljoen MS, Wilson C, Tetrahedron 59:6637, 2003.
28. (b) Azumaya I, Okamoto T, Imabeppu F, Takayanagi H, Heterocycles 60:1419, 2003.
29. (c) Haberhauer G, Rominger F, Tetrahedron Lett 43:6335, 2002.
30. (d) Pattenden G, Thompson T, Tetrahedron Lett 43:2459, 2002.
31. (e) Pohl S, Goddard R, Kubik S, Tetrahedron Lett 42:7555, 2001.
32. (f) Bertram A, Pattenden G, Synlett 1873, 2001.
33. (g) Somogyi L, Haberhauer GH, Rebek J Jr., Tetrahedron 57:1699, 2001.
34. (h) Pattenden G, Thompson T, Chem Commun 717, 2001.
35. (i) Singh Y, Sokolenko N, Kelso MJ, Gahan LR, Abbenante G, Fairlie DP, J Am Chem Soc 123:333, 2001.
36. (j) Bertram A, Pattenden G, Synlett 1519, 2000.
37. (k) Blake AR, Hannam JS, Jolliffe KA, Pattenden G, Synlett 1515, 2000.
38. (l) Bertram A, Hannam JS, Jolliffe KA, de Turiso FG-L, Pattenden G, Synlett 1723, 1999.
39. (m) Sokolenko N, Abbenante G, Scanlon MJ, Jones A, Gahan LR, Hanson GR, Fairlie DP, J Am Chem Soc 121:2603, 1999.
40. (n) Wipf P, Miller CP, J Am Chem Soc 114:10975, 1992.
41. (o) Chen S, Xu J, Tetrahedron Lett 32:6711, 1991.
42. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA Jr., Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, 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, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, Gill PMW, Johnson BG, Chen W, Wong MW, Andres JL, Head-Gordon M, Replogle ES, Pople JA, Gaussian 98 Gaussian, Inc.: Pittsburgh, PA, USA, 1998.
43. Schaftenaat G, Noordik JH, J Comput Aided Mol Design 14:123, 2000.
44. Ames IA, Schmidt MW, Baldrige KK, Boatz JA, Elberts ST, Gordon MS, Jenson JH, Koseki S, Matsunaga N, Nguyen KA, Su SJ, Windus TL, Dupius M, Montgomery JA, J Comput Chem 14:1347, 1993.
45. (a) Wong MW, Frisch MJ, Wiberg KB, J Am Chem Soc 113:4776, 1991.
46. (b) Wong MW, Wiberg KB, Frisch MJ, J Am Chem Soc 114:523, 1993.
47. (c) Wong MW, Wiberg KB, Frisch MJ, J Chem Phys 95:8991, 1991.
48. Supplementary material provided with this article.