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Journal of Physical Organic Chemistry

Volumn 16, Issue 6, 2003, Pages 336-347

Prediction of tautomeric preferences and pKa values for oxyluciferin and its constituent heterocycles

(2) Dahlke, Erin E a Cramer, Christopher J a

a University of Minnesota (United States)

Author keywords

Bioluminescence; Firefly; Oxyluciferin; PKa; Relative energy; Tautomers

Indexed keywords

BIOLUMINESCENCE; ELECTRONIC STRUCTURE; ENZYME KINETICS; ISOMERS; PHASE EQUILIBRIA; SOLUTIONS; THERMODYNAMICS;

TAUTOMERISM;

AROMATIC COMPOUNDS;

EID: 0037937605 PISSN: 08943230 EISSN: None Source Type: Journal
DOI: 10.1002/poc.634 Document Type: Article

Times cited : (16)

References (68)

1
- 0002468820
- Seliger HH, McElroy WD. Proc. Natl. Acad. Sci. USA 1964; 52: 75-81.
- (1964) Proc. Natl. Acad. Sci. USA , vol.52 , pp. 75-81
- Seliger, H.H.¹ McElroy, W.D.²

2
- 0000223359
- Giese AC (ed). Academic Press: New York
- Seliger HH, Motion RA. In Photophysiology, vol. 4, Giese AC (ed). Academic Press: New York, 1968; 253-314.
- (1968) Photophysiology , vol.4 , pp. 253-314
- Seliger, H.H.¹ Motion, R.A.²

3
- 0002552327
- White EH, Rapaport E, Seliger HH, Hopkins TA. Bioorg. Chem. 1971; 1: 92-122.
- (1971) Bioorg. Chem. , vol.1 , pp. 92-122
- White, E.H.¹ Rapaport, E.² Seliger, H.H.³ Hopkins, T.A.⁴

4
- 0003076799
- Suzuki N, Gogo T. Tetrahedron 1972; 28: 4075-4082.
- (1972) Tetrahedron , vol.28 , pp. 4075-4082
- Suzuki, N.¹ Gogo, T.²

5
- 77956986494
- DeLuca M, McElroy WD. Methods Enzymol 1978; 57: 3-36.
- (1978) Methods Enzymol , vol.57 , pp. 3-36
- Deluca, M.¹ McElroy, W.D.²

6
- 0001424344
- White EH, Steinmetz MG, Miano JD, Wildes PD, Morland R. J. Am. Chem. Soc. 1980; 102: 3199-3208.
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 3199-3208
- White, E.H.¹ Steinmetz, M.G.² Miano, J.D.³ Wildes, P.D.⁴ Morland, R.⁵

7
- 0010928512
- Schuster GB. Schmidt SP. Adv. Phys. Org. Chem. 1982; 18: 187-238.
- (1982) Adv. Phys. Org. Chem. , vol.18 , pp. 187-238
- Schuster, G.B.¹ Schmidt, S.P.²

8
- 0003026011
- Campbell AK, Kricka LJ, Stanley PE (eds). Wiley: New York
- McCapra F, Gilfoyle DJ, Young DW, Church NJ, Spencer P. In Bioluminescence and Chemiluminescence, Campbell AK, Kricka LJ, Stanley PE (eds). Wiley: New York, 1994; 387-391.
- (1994) Bioluminescence and Chemiluminescence , pp. 387-391
- McCapra, F.¹ Gilfoyle, D.J.² Young, D.W.³ Church, N.J.⁴ Spencer, P.⁵

9
- 10644240820
- Wood KV. Photochem. Photobiol. 1995; 62: 662-673.
- (1995) Photochem. Photobiol. , vol.62 , pp. 662-673
- Wood, K.V.¹

10
- 0030576862
- Usami K, Isobe M. Tetrahedron 1996; 52: 12061-12090.
- (1996) Tetrahedron , vol.52 , pp. 12061-12090
- Usami, K.¹ Isobe, M.²

11
- 0013270761
- Hastings JW, Kricka LJ, Stanley PE (eds). J Wiley: New York
- McCapra F. In Bioluminescence and Chemiluminescence, Hastings JW, Kricka LJ, Stanley PE (eds). J Wiley: New York, 1997; 7-15.
- (1997) Bioluminescence and Chemiluminescence , pp. 7-15
- McCapra, F.¹

12
- 0345130075
- Wilson T, Hastings JW. Annu. Rev. Cell Biol 1998; 14: 197-230.
- (1998) Annu. Rev. Cell Biol , vol.14 , pp. 197-230
- Wilson, T.¹ Hastings, J.W.²

13
- 0032999438
- Takano Y, Tsunesada T, Isobe H, Yoshioka Y, Yamaguchi K. Saito I. Bull. Chem. Soc. Jpn. 1999; 72: 213-225.
- (1999) Saito I. Bull. Chem. Soc. Jpn. , vol.72 , pp. 213-225
- Takano, Y.¹ Tsunesada, T.² Isobe, H.³ Yoshioka, Y.⁴ Yamaguchi, K.⁵

14
- 0033937250
- McCapra F. Methods Enzymol. 2000; 305: 3-47.
- (2000) Methods Enzymol. , vol.305 , pp. 3-47
- McCapra, F.¹

15
- 0014105802
- Biggley WH, Lloyd JE, Seliger HH. J. Gen. Phys. 1967; 50: 1681-1692.
- (1967) J. Gen. Phys. , vol.50 , pp. 1681-1692
- Biggley, W.H.¹ Lloyd, J.E.² Seliger, H.H.³

16
- 0025412216
- Wood KV. J. Biolum. Chemilum. 1990; 5: 107-114.
- (1990) J. Biolum. Chemilum. , vol.5 , pp. 107-114
- Wood, K.V.¹

17
- 0025879184
- Kajiyama N, Nakano E. Protein Eng. 1991; 4: 691-693.
- (1991) Protein Eng. , vol.4 , pp. 691-693
- Kajiyama, N.¹ Nakano, E.²

18
- 0026083512
- White EH, Roswell DF. Photochem. Photobiol. 1991; 53: 131-136.
- (1991) Photochem. Photobiol. , vol.53 , pp. 131-136
- White, E.H.¹ Roswell, D.F.²

19
- 0027236124
- Gandelman OA, Brovko LY, Ugarova NN, Chikishev AY, Shkurimov AP. J. Photochem. Photobiol. B 1993; 19: 187-191.
- (1993) J. Photochem. Photobiol. B , vol.19 , pp. 187-191
- Gandelman, O.A.¹ Brovko, L.Y.² Ugarova, N.N.³ Chikishev, A.Y.⁴ Shkurimov, A.P.⁵

20
- 0029939559
- Hastings JW. Gene 1996; 173: 5-11.
- (1996) Gene , vol.173 , pp. 5-11
- Hastings, J.W.¹

21
- 0037070540
- Branchini BR, Murtiashaw MH, Magyar RA, Portier NC, Ruggiero MC, Stroh JG. J. Am. Chem. Soc. 2001; 124: 2112-2113.
- (2001) J. Am. Chem. Soc. , vol.124 , pp. 2112-2113
- Branchini, B.R.¹ Murtiashaw, M.H.² Magyar, R.A.³ Portier, N.C.⁴ Ruggiero, M.C.⁵ Stroh, J.G.⁶

22
- 0008711751
- White EH, Wörther H, Field GF, McElroy WD. J. Org. Chem. 1965; 30: 2344-2348.
- (1965) J. Org. Chem. , vol.30 , pp. 2344-2348
- White, E.H.¹ Wörther, H.² Field, G.F.³ McElroy, W.D.⁴

23
- 0001622363
- White EH, Wörther H, Seliger HH, McElroy WD. J. Am. Chem. Soc. 1966; 88: 2015-2019.
- (1966) J. Am. Chem. Soc. , vol.88 , pp. 2015-2019
- White, E.H.¹ Wörther, H.² Seliger, H.H.³ McElroy, W.D.⁴

24
- 0035957085
- Branchini BR, Magyar RA, Murtiashaw MH, Portier NC. Biochemistry 2001; 40: 2410-2418.
- (2001) Biochemistry , vol.40 , pp. 2410-2418
- Branchini, B.R.¹ Magyar, R.A.² Murtiashaw, M.H.³ Portier, N.C.⁴

25
- 0003275864
- Kwiatkowski JS, Zielinski TJ, Rein R. Adv. Quantum Chem. 1986; 18: 85-130.
- (1986) Adv. Quantum Chem. , vol.18 , pp. 85-130
- Kwiatkowski, J.S.¹ Zielinski, T.J.² Rein, R.³

26
- 0001401527
- Karelson MM, Katritzky AR, Szafran M, Zerner MC. J. Org. Chem. 1989; 54: 6030-6034.
- (1989) J. Org. Chem. , vol.54 , pp. 6030-6034
- Karelson, M.M.¹ Katritzky, A.R.² Szafran, M.³ Zerner, M.C.⁴

27
- 0000960089
- Leszczynski J. Chem. Phys. Lett. 1990; 174: 347-354.
- (1990) Chem. Phys. Lett. , vol.174 , pp. 347-354
- Leszczynski, J.¹

28
- 0001170650
- Cramer CJ, Truhlar DG. J. Am. Chem. Soc. 1991; 113: 8552-8553.
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 8552-8553
- Cramer, C.J.¹ Truhlar, D.G.²

29
- 0000761495
- Cramer CJ, Truhlar DG. J. Am. Chem. Soc. 1993; 115: 8810-8817.
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 8810-8817
- Cramer, C.J.¹ Truhlar, D.G.²

30
- 0002537828
- Tapia O, Bertrán J (eds). Kluwer: Dordrecht
- Cramer CJ, Truhlar DG. In Solvent Effects and Chemical Reactivity, Tapia O, Bertrán J (eds). Kluwer: Dordrecht, 1996: 1-81.
- (1996) Solvent Effects and Chemical Reactivity , pp. 1-81
- Cramer, C.J.¹ Truhlar, D.G.²

31
- 2342616849
- Hernández B, Orozco M, Luque FJ. J. Comput.-Aided Mol. Des. 1997: 11: 153-162.
- (1997) J. Comput.-Aided Mol. Des. , vol.11 , pp. 153-162
- Hernández, B.¹ Orozco, M.² Luque, F.J.³

32
- 84962425623
- Luque FJ, López-Bes JM. Cemeli J, Aroztegui M, Orozco M. Theor. Chem. Acc. 1997; 96: 105-113.
- (1997) Theor. Chem. Acc. , vol.96 , pp. 105-113
- Luque, F.J.¹ López-Bes, J.M.² Cemeli, J.³ Aroztegui, M.⁴ Orozco, M.⁵

33
- 0035425779
- Sherer EC, Cramer CJ. J. Comput. Chem. 2001; 22: 1167-1179.
- (2001) J. Comput. Chem. , vol.22 , pp. 1167-1179
- Sherer, E.C.¹ Cramer, C.J.²

34
- 84961985294
- Mennucci B, Toniolo A, Tomasi J. J. Phys. Chem. 2001; 105: 4749-4757.
- (2001) J. Phys. Chem. , vol.105 , pp. 4749-4757
- Mennucci, B.¹ Toniolo, A.² Tomasi, J.³

35
- 0036667456
- Jang YH, Goddard WA, Noyes KT, Sowers LC, Hwang S, Chung DS. Chem. Res. Toxicol. 2002; 15: 1023-1035.
- (2002) Chem. Res. Toxicol. , vol.15 , pp. 1023-1035
- Jang, Y.H.¹ Goddard, W.A.² Noyes, K.T.³ Sowers, L.C.⁴ Hwang, S.⁵ Chung, D.S.⁶

36
- 0344532508
- Pullman B, Pullman A. Adv. Heterocycl. Chem. 1971; 13: 77-136.
- (1971) Adv. Heterocycl. Chem. , vol.13 , pp. 77-136
- Pullman, B.¹ Pullman, A.²

37
- 0017148262
- Topal MD, Fresco JR. Nature (London) 1976; 263: 285-287.
- (1976) Nature (London) , vol.263 , pp. 285-287
- Topal, M.D.¹ Fresco, J.R.²

38
- 0025197061
- Bashford D, Karplus M. Biochemistry 1990; 29: 10219-10225.
- (1990) Biochemistry , vol.29 , pp. 10219-10225
- Bashford, D.¹ Karplus, M.²

39
- 0030000527
- Schüürmann G. Quant. Struct.-Act Relat. 1996; 15: 121-132.
- (1996) Quant. Struct.-Act Relat. , vol.15 , pp. 121-132
- Schüürmann, G.¹

40
- 0031358013
- Topol IA, Tawa GJ, Burt SK, Rashin AA. J. Phys. Chem. A 1997; 101: 10075-10081.
- (1997) J. Phys. Chem. A , vol.101 , pp. 10075-10081
- Topol, I.A.¹ Tawa, G.J.² Burt, S.K.³ Rashin, A.A.⁴

41
- 84961981091
- Cramer CJ, Truhlar DG. Chem. Rev. 1999; 99: 2161-2200.
- (1999) Chem. Rev. , vol.99 , pp. 2161-2200
- Cramer, C.J.¹ Truhlar, D.G.²

42
- 84962440579
- Richardson WH, Peng C, Bashford D, Noodleman L, Case DA. Int. J. Quantum Chem. 1997; 61: 207-217.
- (1997) Int. J. Quantum Chem. , vol.61 , pp. 207-217
- Richardson, W.H.¹ Peng, C.² Bashford, D.³ Noodleman, L.⁴ Case, D.A.⁵

43
- 84961974409
- Gross KC, Seybold PG, Feldgus S, Shields GC.
- Liptak MD. Gross KC, Seybold PG, Feldgus S, Shields GC. J. Am. Chem. Soc. 2002; 124: 6421-6427.
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 6421-6427
- Liptak, M.D.¹

44
- 0037149134
- Klicic JJ, Friesner RA, Liu SY, Guida WC. J. Phys. Chem. A 2002; 106: 1327-1335.
- (2002) J. Phys. Chem. A , vol.106 , pp. 1327-1335
- Klicic, J.J.¹ Friesner, R.A.² Liu, S.Y.³ Guida, W.C.⁴

45
- 0037104738
- Chipman DM. J. Phys. Chem. A 2002; 106: 7413-7422.
- (2002) J. Phys. Chem. A , vol.106 , pp. 7413-7422
- Chipman, D.M.¹

46
- 0003395607
- Wiley: Chichester
- Cramer CJ. Essentials of Computational Chemistry: Theories and Models. Wiley: Chichester, 2002; pp 319-345.
- (2002) Essentials of Computational Chemistry: Theories and Models , pp. 319-345
- Cramer, C.J.¹

47
- 33645898818
- Perdew J, Wang Y. Phys. Rev. B 1992; 45: 13244-13249.
- (1992) Phys. Rev. B , vol.45 , pp. 13244-13249
- Perdew, J.¹ Wang, Y.²

48
- 0031592439
- Burke K, Ernzerhof M, Perdew JP. Chem. Phys. Lett. 1997; 265: 115-120.
- (1997) Chem. Phys. Lett. , vol.265 , pp. 115-120
- Burke, K.¹ Ernzerhof, M.² Perdew, J.P.³

49
- 0002017297
- Dobson JF, Vignale G, Das MP (eds). Plenum Press: New York
- Burke K, Perdew JP, Wang Y. In Electronic Density Functional Theory. Recent Progress and New Directions, Dobson JF, Vignale G, Das MP (eds). Plenum Press: New York, 1998; 81-121.
- (1998) Electronic Density Functional Theory. Recent Progress and New Directions , pp. 81-121
- Burke, K.¹ Perdew, J.P.² Wang, Y.³

50
- 11244326290
- Adamo C, Barone V. J. Chem. Phys. 1998; 108: 664-675.
- (1998) J. Chem. Phys. , vol.108 , pp. 664-675
- Adamo, C.¹ Barone, V.²

51
- 84873055189
- Wiley: New York
- Hehre WJ, Radom L, Schleyer PvR. Pople JA. Ab Initio Molecular Orbital Theory. Wiley: New York, 1986.
- (1986) Ab Initio Molecular Orbital Theory
- Hehre, W.J.¹ Radom, L.² Schleyer, Pvr.³ Pople, J.A.⁴

52
- 0034225915
- Fast PL, Truhlar DG. J. Phys. Chem. A 2000; 104: 6111-6116.
- (2000) J. Phys. Chem. A , vol.104 , pp. 6111-6116
- Fast, P.L.¹ Truhlar, D.G.²

53
- 0038225772
- Article 14
- Tratz CM, Fast PL, Truhlar DG. Phys. Chem. Commun. 1999; 2: Article 14.
- (1999) Phys. Chem. Commun. , vol.2
- Tratz, C.M.¹ Fast, P.L.² Truhlar, D.G.³

54
- 0001317989
- Fast PL, Sanchez ML, Truhlar DG. Chem. Phys. Lett. 1999; 306: 407-410.
- (1999) Chem. Phys. Lett. , vol.306 , pp. 407-410
- Fast, P.L.¹ Sanchez, M.L.² Truhlar, D.G.³

55
- 0003838469
- Wiley-VCH: Weinheim
- Koch W, Holthausen MC. A Chemist's Guide to Density Functional Theory. Wiley-VCH: Weinheim, 2000.
- (2000) A Chemist's Guide to Density Functional Theory
- Koch, W.¹ Holthausen, M.C.²

56
- 0000188281
- Easton RE, Giesen DJ, Welch A, Cramer CJ, Truhlar DG. Theor. Chim. Acta 1996; 93: 281-301.
- (1996) Theor. Chim. Acta , vol.93 , pp. 281-301
- Easton, R.E.¹ Giesen, D.J.² Welch, A.³ Cramer, C.J.⁴ Truhlar, D.G.⁵

57
- 33746614482
- Dunning TH. J. Chem. Phys. 1989; 90: 1007-1023.
- (1989) J. Chem. Phys. , vol.90 , pp. 1007-1023
- Dunning, T.H.¹

58
- 4143095330
- Kendall RA, Dunning TH, Harrison RJ. J. Chem. Phys. 1992; 96: 6796-6806.
- (1992) J. Chem. Phys. , vol.96 , pp. 6796-6806
- Kendall, R.A.¹ Dunning, T.H.² Harrison, R.J.³

59
- 3843146349
- Woon DE, Dunning TH. J. Chem. Phys. 1993; 98: 1358-1371.
- (1993) J. Chem. Phys. , vol.98 , pp. 1358-1371
- Woon, D.E.¹ Dunning, T.H.²

60
- 0012154673
- Curtiss LA, Raghavachari K, Redfern PC, Rassolov V, Pople JA. J. Chem. Phys. 1998; 109: 7764-7780.
- (1998) J. Chem. Phys. , vol.109 , pp. 7764-7780
- Curtiss, L.A.¹ Raghavachari, K.² Redfern, P.C.³ Rassolov, V.⁴ Pople, J.A.⁵

61
- 0001440875
- Zhu T, Li J, Hawkins GD, Cramer CJ, Truhlar DG. J. Chem. Phys. 1998; 109: 9117-9133.
- (1998) J. Chem. Phys. , vol.109 , pp. 9117-9133
- Zhu, T.¹ Li, J.² Hawkins, G.D.³ Cramer, C.J.⁴ Truhlar, D.G.⁵

62
- 0000958036
- Li J, Zhu T, Cramer CJ, Truhlar DG. J. Phys. Chem. A 1998; 102: 1820-1831.
- (1998) J. Phys. Chem. A , vol.102 , pp. 1820-1831
- Li, J.¹ Zhu, T.² Cramer, C.J.³ Truhlar, D.G.⁴

64
- 0003681075
- University of Minnesota: Minneapolis, MN
- Xidos JD, Li J, Thompson JD, Hawkins GD. Winget PD, Zhu T, Rinaldi D, Liotard DA, Cramer CJ, Truhlar DG, Frisch MJ. MNGSM, Version 1.8. University of Minnesota: Minneapolis, MN, 2001.
- (2001) MNGSM, Version 1.8
- Xidos, J.D.¹ Li, J.² Thompson, J.D.³ Hawkins, G.D.⁴ Winget, P.D.⁵ Zhu, T.⁶ Rinaldi, D.⁷ Liotard, D.A.⁸ Cramer, C.J.⁹ Truhlar, D.G.¹⁰ Frisch, M.J.¹¹

65
- 0009015575
- University of Minnesota: Minneapolis, MN
- Rodgers JM, Lynch BJ, Fast PL, Chuang Y-Y, Pu J, Truhlar DT. MULTILEVEL. University of Minnesota: Minneapolis, MN, 2000.
- (2000) Multilevel
- Rodgers, J.M.¹ Lynch, B.J.² Fast, P.L.³ Chuang, Y.-Y.⁴ Pu, J.⁵ Truhlar, D.T.⁶

66
- 0036791051
- Kormos BL, Cramer CJ. J. Phys. Org. Chem. 2002; 15: 712-720.
- (2002) J. Phys. Org. Chem. , vol.15 , pp. 712-720
- Kormos, B.L.¹ Cramer, C.J.²

67
- 0037550338
- submitted for publication
- Lewis A, Bumpus JA, Truhlar DG, Cramer CJ. J. Chem. Educ. submitted for publication.
- J. Chem. Educ.
- Lewis, A.¹ Bumpus, J.A.² Truhlar, D.G.³ Cramer, C.J.⁴

68
- 0003998388
- CRC Press: Boca Raton, FL, section 8
- Lide DR (ed). CRC Handbook of Chemistry and Physics. CRC Press: Boca Raton, FL, 1995; section 8, p 64.
- (1995) CRC Handbook of Chemistry and Physics , pp. 64
- Lide, D.R.¹

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