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Stepwise approach toward first generation nonenzymatic hydrolases

(1998) JOURNAL OF ORGANIC CHEMISTRY. 63(8). p.2548-2559
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Abstract
The synthesis and reactivity study of a first generation serine protease mimic is described. Central in the design stands the possibility of stabilization of the transition state by an amino triol such as 8t. En route to 8t, a series of amino alcohols (4-8) was obtained, the reactivity of which was studied toward esterification by acetylimidazole (AcIm) and by p-nitro-2,2,2-trifluoroacetanilide (PNTFA). Interesting reactivity differences were observed between the cis-and the trans-series, especially between 7c and 7t (AcIm), and between 8c and 8t (PNTFA). In both cases the results are explained by invoking extra stabilization of the tetrahedral oxyanion.
Keywords
BETA-UNSATURATED KETONES, ALPHA, ANCHORING SUBSTITUTION, PROTEOLYTIC-ENZYMES, NITROPHENYL ACETATE, ARTIFICIAL ENZYMES, 1, 3-AMINO ALCOHOLS, SERINE PROTEASES, CYCLIC-PEPTIDES, AMINO ALCOHOLS, MODELS

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Citation

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Chicago
Madder, Annemieke, Pierre De Clercq, and Jean-Paul Declercq. 1998. “Stepwise Approach Toward First Generation Nonenzymatic Hydrolases.” Journal of Organic Chemistry 63 (8): 2548–2559.
APA
Madder, A., De Clercq, P., & Declercq, J.-P. (1998). Stepwise approach toward first generation nonenzymatic hydrolases. JOURNAL OF ORGANIC CHEMISTRY, 63(8), 2548–2559.
Vancouver
1.
Madder A, De Clercq P, Declercq J-P. Stepwise approach toward first generation nonenzymatic hydrolases. JOURNAL OF ORGANIC CHEMISTRY. 1998;63(8):2548–59.
MLA
Madder, Annemieke, Pierre De Clercq, and Jean-Paul Declercq. “Stepwise Approach Toward First Generation Nonenzymatic Hydrolases.” JOURNAL OF ORGANIC CHEMISTRY 63.8 (1998): 2548–2559. Print.
@article{177679,
  abstract     = {The synthesis and reactivity study of a first generation serine protease mimic is described. Central in the design stands the possibility of stabilization of the transition state by an amino triol such as 8t. En route to 8t, a series of amino alcohols (4-8) was obtained, the reactivity of which was studied toward esterification by acetylimidazole (AcIm) and by p-nitro-2,2,2-trifluoroacetanilide (PNTFA). Interesting reactivity differences were observed between the cis-and the trans-series, especially between 7c and 7t (AcIm), and between 8c and 8t (PNTFA). In both cases the results are explained by invoking extra stabilization of the tetrahedral oxyanion.},
  author       = {Madder, Annemieke and De Clercq, Pierre and Declercq, Jean-Paul},
  issn         = {0022-3263},
  journal      = {JOURNAL OF ORGANIC CHEMISTRY},
  keywords     = {BETA-UNSATURATED KETONES,ALPHA,ANCHORING SUBSTITUTION,PROTEOLYTIC-ENZYMES,NITROPHENYL ACETATE,ARTIFICIAL ENZYMES,1,3-AMINO ALCOHOLS,SERINE PROTEASES,CYCLIC-PEPTIDES,AMINO ALCOHOLS,MODELS},
  language     = {eng},
  number       = {8},
  pages        = {2548--2559},
  title        = {Stepwise approach toward first generation nonenzymatic hydrolases},
  url          = {http://dx.doi.org/10.1021/jo971935+},
  volume       = {63},
  year         = {1998},
}

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