On the significance of the trigger reaction in the action of the calicheamicin γI1 anti-cancer drug

Theoretical Chemistry Accounts

Volumn 97, Issue 1-4, 1997, Pages 203-210

  Lindh, Roland ^a   Ryde, Ulf ^a   Schütz, Martin ^a  

^a CHEMICAL CENTER   (Sweden)

Author keywords

Bergman reaction; Calicheamicin; Integral direct MP2; Parallel MP2; Trigger reaction

Indexed keywords

EID: 0031285827     PISSN: 1432881X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s002140050254     Document Type: Article

References (37)

1. Walker S, Murnick J, Kahne D (1993) J Am Chem Soc 115:7954
2. Paloma LG, Smith JA, Chazin WJ, Nicolaou KC (1994) J Am Chem Soc 116:3697
3. Langley DR, Golik J, Krishnan B, Doyle TW, Beveridge DL (1994) J Am Chem Soc 116:15
4. Koga N, Morokuma K (1991) J Am Chem Soc 113:1907
5. Kraka E, Cremer D (1993) Chem Phys Lett 216:333
6. Nicolaides A, Borden WT (1993) J Am Chem Soc 115:11951
7. Lindh R, Persson BJ (1994) J Am Chem Soc 116:4363
8. Kraka E, Cremer D (1994) J Am Chem Soc 116:4929
9. Lindh R, Lee TJ, Bernhardsson A, Persson BJ, Karlström G (1995) J Am Chem Soc 117:7186
10. Lindh R, Schütz M (1996) Chem Phys Letters 258:409
11. Roth WR, Hopf H, Horn C (1994) Chem Ber 127:1765
12. Wenthold PG, Squires RR (1994) J Am Chem Soc 116:6401
13. Jones RR, Bergman RG (1972) J Am Chem Soc 94:660
14. Bergman RG (1973) Acc Chem Res 9:25
15. Lockhart TP, Comita PB, Bergman RG (1981) J Am Chem Soc 103:4082
16. Lockhart TP, Bergman RG (1981) J Am Chem Soc 103:4090
17. Chang NY, Yu C-H (1995) Poster at the "Molecular Quantum Mechanics: Methods and Applications" conference 3-7 September 1995 in Cambridge, England, the activation energy of the Bergman autoaromatization of (Z)-hex-3-ene-1,5-diyne, (Z)-hept-4-ene-2,6-diyne, (Z)-oct-4-ene-2,6-diyne, and cyclodec-3-ene-1,5-diyne computed at the MP2/6-31G**//MP2/6-31G* amounts to 23.06, 23.56, 24.26, and 16.55 kcal/mol, respectively
18. Nicolaou KC, Zuccarello G, Ogawa Y, Schweiger EJ, Kumazawa T (1988) J Am Chem Soc 110:4866
19. Nicolaou KC, Smith AL (1992) Ace Chem Res 25:497
20. Maier ME (1995) Synlett p 13
21. Snyder JP (1989) J Am Chem Soc 111:7630
22. Magnus P, Fortt S, Pitterna T, Snyder JP (1990) J Am Chem Soc 112:4986
23. Snyder JP (1990) J Am Chem Soc 112:5367
24. Magnus P, Fairhurst RA (1994) J Chem Soc Chem Commun p 1541
25. De Voss JJ, Hangeland JJ, Townsend CA (1990) J Am Chem Soc 112:4554
26. 1/2 = ln2/k
27. Bredt's rule: a bridgehead carbon atom cannot participate in a double bond formation. This is a rule that have proven valid for at least most five- and six-membered rings
28. Bredt J (1924) Liebig's Ann d Chem 437:1
29. Becke AD (1988) Phys Rev A 38:3098
30. Perdew JP (1986) Phys Rev B 33:8822
31. Frisch MJ, Trucks GW, Schlegel HB, Gill PMW, Johnson BG, Robb MA, Cheeseman JR, Keith T, Petersson GA, Montgomery JA, Raghavachari K, Al-Laham MA, Zakrzewski VG, Ortiz JV, Foresman JB, Cioslowski J, Stefanov BB, Nanayakkara A, Challacombe M, Peng CY, Ayala PY, Chen W, Wong MW, Andres JL, Replogle ES, Gomperts R, Martin RL, Fox DJ, Binkley JS, Defrees DJ, Baker J, Stewart JP, Head-Gordon M, Gonzalez C, Pople JA (1995) Gaussian 94 revision D.1. Gaussian, Inc., Pittsburgh, Pa
32. Pierloot K, Dumez B, Widmark P.-O, Roos BO (1995) Theor Chim Acta 90:87
33. Schütz M, Lindh R (1997) Theor Chim Acta 95:13
34. Andersson K, Blomberg MRA, Fülscher MP, Karlström G, Kellö V, Lindh R, Malmqvist P.-Å, Noga J, Olsen J, Roos BO, Sadlej AJ, Schütz M, Seijo L, Siegbahn PEM, Urban M, Widmark P.-O (1996) MOLCAS version 4, experimental version. Dept of Theor Chem, Chem Center, Univ of Lund, POB 124, S-221 00 Lund
35. Davico GE, Bierbaum VM, DePuy CH, Ellison GB, Squires RR (1995) J Am Chem Soc 117:2590
36. Veng-Pedersen P (1989) Clin Pharmacokinet 17:345
37. Veng-Pedersen P (1989) Clin Pharmacokinet 17:424