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Volumn 108, Issue 52, 2004, Pages 11740-11751

Conformational preferences in the transition states and tetrahedral intermediates of transacylations. Relationships to enzyme-bound conformations of phosphonate inhibitors of lipases and esterases

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; CATALYSIS; CONFORMATIONS; CRYSTAL STRUCTURE; ENZYMES; HYDROLYSIS; X RAY ANALYSIS;

EID: 84961981093     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp045889a     Document Type: Article
Times cited : (9)

References (110)
  • 72
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    • note
    • 2 of serine is ∼16. However, our purpose is to explore the relationship on the conformational preferences of the transition states and intermediates in transacylation to the phosphonate inhibitors. The proton transfer, itself, would not affect the conformational preference of the transacylation, because, in the transition state, the proton becomes attached to histidine.
  • 83
    • 84962353268 scopus 로고    scopus 로고
    • note
    • N2) reaction path for the transacylation of methyl acetate. The activation free energies for the concerted pathway are 3.9, 10.7, and 17.1 kcal/mol in the gas phase, protein, and water, therefore, the stepwise mechanism via tetrahedral intermediate was favored to the concerted one.
  • 84
    • 40849151148 scopus 로고
    • (a) Sutor, D. J. Nature 1962, 195, 68-69.
    • (1962) Nature , vol.195 , pp. 68-69
    • Sutor, D.J.1
  • 86
    • 0000216832 scopus 로고    scopus 로고
    • (c) Desiraju, G. R. Acc. Chem. Res. 1996, 29, 441-449.
    • (1996) Chem. Res. , vol.29 , pp. 441-449
    • Acc, D.G.R.1
  • 94
    • 0038077306 scopus 로고    scopus 로고
    • The definitions of the conformations of these papers are different from ours
    • (d) Venkatesan, V.; Sundararajan, K.; Viswanathan, K. S. Spectrochim. Acta A 2003, 59, 1497-1507. The definitions of the conformations of these papers are different from ours.
    • (2003) Spectrochim. Acta A , vol.59 , pp. 1497-1507
    • Venkatesan, V.1    Sundararajan, K.2    Viswanathan, K.S.3
  • 96
    • 0011083499 scopus 로고    scopus 로고
    • -) and σ*(C-OMe) are 5-6 and 4-5 kcal/mol, respectively (see Table SI), (a) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Reu. 1988, 88, 899-926. (b) Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO 4.M.; Theoretical Chemistry Institute, University of Wisconsin: Madison, WI.
    • (1988) Chem. Reu. , vol.88 , pp. 899-926
    • Reed, A.E.1    Curtiss, L.A.2    Weinhold, F.3
  • 97
    • 0011083499 scopus 로고    scopus 로고
    • Theoretical Chemistry Institute, University of Wisconsin: Madison, WI
    • -) and σ*(C-OMe) are 5-6 and 4-5 kcal/mol, respectively (see Table SI), (a) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Reu. 1988, 88, 899-926. (b) Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO 4.M.; Theoretical Chemistry Institute, University of Wisconsin: Madison, WI.
    • NBO 4.M
    • Glendening, E.D.1    Badenhoop, J.K.2    Reed, A.E.3    Carpenter, J.E.4    Weinhold, F.5
  • 106
    • 84962412371 scopus 로고    scopus 로고
    • note
    • 3) are similar to those of others, because of the large CH⋯O distances (2.6-2.8 Å); consequently, the CH⋯O hydrogen bonds are negligible.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.