The use of isotopes in the study of reactions of acyl, phosphoryl, and sulfuryl esters

Journal of Labelled Compounds and Radiopharmaceuticals

Volumn 50, Issue 11-12, 2007, Pages 1026-1038

  Hoff, Richard H ^a   Hengge, Alvan C ^b  

^a UNITED STATES MILITARY ACADEMY   (United States)

^b UTAH STATE UNIVERSITY   (United States)

Author keywords

Amide; Ester; Kinetic isotope effect; Phosphate ester; Solvent isotope effect; Sulfate ester

Indexed keywords

AMIDES; ESTERS; NUCLEIC ACIDS; SULFUR COMPOUNDS;

ACYL TRANSFER REACTION; BIOCHEMICAL PATHWAY; COMMERCIAL CHEMICALS; KINETIC ISOTOPES EFFECTS; PHOSPHATE ESTERS; PHOSPHORYL TRANSFER REACTIONS; PROTEIN-NUCLEIC ACIDS; SOLVENT ISOTOPE EFFECTS; SULFATE ESTERS; SULFURYL TRANSFER REACTIONS;

ISOTOPES;

ACYL ESTER; ALKALINE PHOSPHATASE; CALCINEURIN; ESTER DERIVATIVE; ISOTOPE; OXYGEN 18; PHOSPHATASE; PHOSPHORYL ESTER; PHOSPHOTRIESTERASE; PROTEIN TYROSINE PHOSPHATASE; SULFATE; SULFURYL ESTER; UNCLASSIFIED DRUG;

BIOCHEMISTRY; CATALYSIS; CHEMICAL BINDING; CHEMICAL BOND; CHEMICAL REACTION; CONCENTRATION (PARAMETERS); ENZYME ACTIVITY; EQUILIBRIUM CONSTANT; HYBRIDIZATION; HYDROLYSIS; KINETICS; PROTON TRANSPORT; REVIEW; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

EID: 38349071759     PISSN: 03624803     EISSN: 10991344     Source Type: Journal    
DOI: 10.1002/jlcr.1433     Document Type: Review

References (103)

1. Bennet AJ, Brown RS. Physical organic chemistry of acyl transfer reactions. In Comprehensive Biological Catalysis: A Mechanistic Reference, vol. 1, Sinnott M (ed.). Academic Press: New York, 1997; 293-326;
2. Brown RS, Bennet AJ, Slebockatilk H. Accounts Chem Res 1992; 25: 481-488.
3. 2- group. In Comprehensive Biological Catalysis: A Mechanistic Reference, vol. 1. Sinnott M (ed.). Academic Press: San Diego, CA, 1998; 517-542.
4. Hengge AC. Adv Phys Org Chem 2005; 40: 49-108;
5. Thatcher GRJ, Kluger R. Adv Phys Org Chem 1989; 25: 99-265.
6. Chapman E, Best MD, Hanson SR, Wong CH. Angew Chem, Int Ed Engl 2004; 43: 3526-3548;
7. VI: sulfotransferases. In Comprehensive Biological Catalysis: A Mechanistic Reference, vol. 1. Sinnott M (ed.). Academic Press: San Diego, CA, 1998; 627-635.
8. Kresge AJ. Pure Appl Chem 1964; 8: 243;
9. Quinn DM. Theory and practice of solvent isotope effects. In Isotope Effects in Chemistry and Biology, Kohen A, Limbach H-H (eds). Taylor & Francis: New York, 2006; 995-1018;
10. Schowen KB, Schowen RL. Methods Enzymol 1982; 87C: 551-606.
11. Marlier JF. Acc Chem Res 2001; 34: 283-290.
12. Northrop DB. Determining the absolute magnitude of hydrogen isotope effects. In Isotope Effects on Enzyme-Catalyzed Reactions, Cleland WW, O'Leary MH, Northrop DB (eds). University Park Press: Baltimore, MD, 1977; 122-152.
13. Melander L, Saunders WH. Reaction Rates of Isotopic Molecules. Robert E. Krieger Malabar, FL, 1987.
14. Rishavy MA, Cleland WW. Con J Chem 1999; 77: 967-977.
15. Parkin DW. Methods for the determination of competitive and noncompetitive kinetic isotope effects. In Enzyme Mechanism from Isotope Effects, Cook PF (ed.). CRC Press: Boca Raton, FL, 1991; 269-290;
16. Singleton DA, Thomas AA. J Am Chem Soc 1995; 121: 9357-9358.
17. Kiick DM. Use of the stable isotope remote label technique to determine isotope effects in enzyme-catalyzed reactions. In Enzyme Mechanism from Isotope Effects, Cook PF (ed.). CRC Press: Boca Raton, FL, 1991; 313-330.
18. O'Leary MH, Marlier JF. J Am Chem Soc 1979; 101: 3300-3306.
19. Bender ML. Chem Rev 1960; 60: 53-113;
20. Shain SA, Kirsch JF. J Am Chem Soc 1968; 90: 5848-5854;
21. Johnson SL. Adv Phys Org Chem 1967; 5: 237-330;
22. O'Connor CJ. Q Rev Chem Soc 1971; 24: 553-564;
23. Jencks WP. Chem Rev 1972; 72: 705-718.
24. Bender ML, Dewey RS. J Am Chem Soc 1956; 78: 317-319;
25. Polanyi M, Szabo AL. Trans Faraday Soc 1934; 30: 508-512.
26. Bentley TW, Carter GE, Harris HC. J Chem Soc Perkin Trans 2 1985; 983-990;
27. Bentley TW, Koo S. J Chem Soc Perkin Trans 2 1989; 1385-1392.
28. Kellogg BA, Tse JE, Brown RS. J Am Chem Soc 1995; 117: 1731-1735.
29. Sawyer CB, Kirsch JF. J Am Chem Soc 1973; 95: 7375-7381.
30. Bilkadi Z, de Lorimier R, Kirsch JF. J Am Chem Soc 1975; 97: 4317-4322.
31. Kirsch JF. Secondary kinetic isotope effects. In Isotope Effects on Enzyme-Catalyzed Reactions, Cleland WW, O'Leary MH, Northrop DB (eds). University Park Press: Baltimore, MD, 1977; 100-121.
32. Marlier JF. J Am Chem Soc 1993; 115: 5953-5956.
33. Stefanidis D, Jencks WP. J Am Chem Soc 1993; 115: 6045-6050.
34. Marlier JF, O'Leary MH. J Org Chem 1981; 46: 2175-2177.
35. Satterthwait AC, Jencks WP. J Am Chem Soc 1974; 96: 7018-7031.
36. Marlier JF, Haptonstall BA, Johnson AJ, Sacksteder KA. J Am Chem Soc 1997; 119: 8838-8842.
37. Ba-Saif S, Colthurst M, Waring MA, Williams A. J Chem Soc Perkin Trans 2 1991; 1901-1908;
38. Ba-Saif S, Luthra AK, Williams A. J Am Chem Soc 1987; 109: 6362-6368;
39. Ba-Saif S, Luthra AK, Williams A. J Am Chem Soc 1989; 111: 2647-2652;
40. Stefanidis D, Cho S, Dhe-Paganon S, Jencks WP. J Am Chem Soc 1993; 115: 1650-1656.
41. Guthrie JP. J Am Chem Soc 1991; 113: 6045-6050;
42. Tantillo DJ, Houk KN. J Org Chem 1999; 64: 3066-3076.
43. Xie D, Zhou Y, Xu D, Guo H. Org Lett 2005; 7: 2093-2095.
44. Buncel E, Um IH, Hoz S. J Am Chem Soc 1989; 111: 971-975;
45. Kwon DS, Lee GJ, Um IH. Bull Korean Chem Soc 1990; 11: 262-265.
46. Hogg JL, Rodgers J, Kovach I, Schowen RL. J Am Chem Soc 1980; 102: 79-85;
47. Kovach IM, Hogg JL, Raben T, Halbert K, Rodgers J, Schowen RL. J Am Chem Soc 1980; 102: 1991-1999.
48. Hess RA, Hengge AC. J Am Chem Soc 1994; 116: 11256-11263.
49. Hess RA, Hengge AC, Cleland WW. J Am Chem Soc 1998; 120: 2703-2709.
50. Biechler S, Taft Jr RW. J Am Chem Soc 1957; 79: 4927-4935;
51. Schowen RL, Jayarmann H, Kershner L. J Am Chem Soc 1966; 88: 3373-3375.
52. Marlier JF, Dopke NC, Johnstone KR, Wirdzig TJ. J Am Chem Soc 1999; 121: 4356-4363.
53. SlebockaTilk H, Rescorla CG, Shirin S, Bennet AJ, Brown RS. J Am Chem Soc 1997; 119: 10969-10975.
54. Slebocka-Tilk H, Neverov AA, Brown RS. J Am Chem Soc 2003; 125: 1851-1858.
55. Stein RL, Fujihara H, Quinn DM, Fischer G, Kullertz G, Barth A, Schowen RL. J Am Chem Soc 1984; 106: 1457-1461.
56. Slebocka-Tilk H, Sauriol F, Monette M, Brown RS. Can J Chem 2002; 80: 1343-1350.
57. Hengge AC, Stein RL. Biochemistry 2004; 43: 742-747.
58. Huskey WP. Origin and interpretations of heavy-atom isotope effects. In Enzyme Mechanism From Isotope Effects, Cook PF (ed.). CRC Press: Boca Raton, FL, 1991; 37-72.
59. Melander L, Saunders WH. Secondary hydrogen isotope effects: α-deuterium. In Reaction Rates of Isotopic Molecules. Wiley: New York, 1980; 172-174.
60. Abott SJ, Jones SR, Weinman SA, Bockhoff FM, McLafferty FW, Knowles JR. J Am Chem Soc 1979; 101: 4323-4332;
61. Cullis PM, Lowe G. J Chem Soc Chem Commun 1978; 512-514;
62. Cullis PM, Lowe G. J Chem Soc Perkin Trans 1 1981; 1: 2317-2321.
63. Arnold JRP, Bethell RC, Lowe G. Bioorg Chem 1987; 15: 250-261;
64. Cullis PM, Iagrossi A. J Am Chem Soc 1986; 108: 7870-7871;
65. Richard JP, Prasher DC, Ives DH, Frey PA. J Biol Chem 1979; 254: 4339-4341.
66. Kirby AJ, Varvoglts AG. J Am Chem Soc 1967; 89: 415-423.
67. Herschlag D, Jencks WP. J Am Chem Soc 1989; 111: 7579-7586.
68. Hengge AC. Acc Chem Res 2002; 35: 105-112.
69. Gorenstein DG, Lee Y-G, Kar D. J Am Chem Soc 1977; 99: 2264-2267.
70. Hengge AC, Edens WA, Elsing H. J Am Chem Soc 1994; 116: 5045-5049.
71. Khan SA, Kirby AJ. J Chem Soc (B) 1970; 1172-1182.
72. Kirby AJ, Younas M. J Chem Soc (B) 1970; 510-513.
73. Cleland WW, Hengge AC. FASEB J 1995; 9: 1585-1594.
74. Cassano AG, Anderson VE, Harris ME. J Am Chem Soc 2002; 124: 10964-10965.
75. Hall CR, Inch TD. Tetrahedron 1980; 36: 2059-2095.
76. Anderson MA, Shim H, Raushel FM, Cleland WW. J Am Chem Soc 2001; 123: 9246-9253.
77. Catrina I, O'Brien PJ, Purcell J, Nikolic-Hughes I, Zalatan JG, Hengge AC, Herschlag D. J Am Chem Soc 2007; 129: 5760-5765.
78. Zhang Z-Y. CRC Crit Rev Biochem Mol Biol 1998; 33: 1-52.
79. Fauman EB, Yuvaniyama C, Schubert H, Stuckey JA, Saper MA. J Biol Chem 1996; 217: 18780-18788;
80. Stuckey JA, Schubert HL, Fauman EB, Zhang Z-Y, Dixon JE, Saper MA. Nature 1994; 370: 571-575.
81. Hengge AC, Sowa GA, Wu L, Zhang Z-Y. Biochemistry 1995; 34: 13982-13987.
82. Hengge AC, Denu JM, Dixon JE. Biochemistry 1996; 35: 7084-7092.
83. Hengge AC, Zhao Y, Wu L, Zhang Z-Y. Biochemistry 1997; 36: 7928-7936.
84. Rusnak F, Mertz P. Physiol Rev 2000; 80: 1483-1521.
85. Hengge AC, Martin BL. Biochemistry 1997; 36: 10185-10191.
86. Martin B, Pallen C, Wang J, Graves D. J Biol Chem 1985; 260: 14932-14937.
87. Mertz P, Yu L, Sikkink R, Rusnak F. J Biol Chem 1997; 272: 21296-21302;
88. Hoff RH, Mertz P, Rusnak F, Hengge AC. J Am Chem Soc 1999; 121: 6382-6390.
89. Raushel FM. Curr Opin Microbiol 2002; 5: 288-295.
90. Vanhooke JL, Benning MM, Raushel FM, Holden HM. Biochemistry 1996; 35: 6020-6025.
91. Lewis VE, Donarski WJ, Wild JR, Raushel FM. Biochemistry 1988; 27: 1591-1597.
92. Caldwell SR, Newcomb JR, Schlecht KA, Raushel FM. Biochemistry 1991; 30: 7438-7444.
93. Caldwell SR, Raushel FM, Weiss PM, Cleland WW. Biochemistry 1991; 30: 7444-7450.
94. Benkovic SJ, Benkovic PA. J Am Chem Soc 1966; 88: 5504-5511.
95. Garner HK, Lucas HJ. J Am Chem Soc 1950; 72: 5497-5501;
96. Kaiser ET, Panar M, Westheimer FH. J Am Chem Soc 1963; 85: 602-607.
97. Fendler EJ, Fendler JH. J Org Chem 1968; 33: 3852-3859.
98. Chai CLL, Hepburn TW, Lowe G. J Chem Soc. Chem Commun 1991; 19: 1403-1405.
99. Kice JL, Anderson JM. J Am Chem Soc 1966; 88: 5242-5245.
100. Hoff RH, Larsen P, Hengge AC. J Am Chem Soc 2001; 123: 9338-9344.
101. Burlingham BT, Pratt LM, Davidson ER, Shiner VJJ, Fong J, Widlanski TS. J Am Chem Soc 2003; 125: 13036-13037.
102. Younker JM, Hengge AC. J Org Chem 2004; 69: 9043-9048.
103. Hoff RH, Czyryca PG, Sun M, Leyh TS, Hengge AC. J Biol Chem 2006; 281: 30645-30649.