Antibody Catalysis of BAc2 Aryl Carbamate Ester Hydrolysis:  A Highly Disfavored Chemical Process.  J. Am. Chem. Soc. 1997, 119, 2315−2316

Wentworth, Paul; Datta, Anita; Smith, Simon N.; Marshall, Ann; Partridge, and Lynda J.; Blackburn, G. Michael

doi:10.1021/ja975404e

Cited by 7 publications

(9 citation statements)

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“…[4b] the efficiency of antibody catalysis [15] could be reached in the case of carbamate hydrolysis. These new catalysts are very promising for broad application since in contrast to antibodies molecularly imprinted polymers show a much higher chemical, mechanical, and thermal stability, can easily be prepared, and have the potential of simple variation of structure.…”

Section: Methodsmentioning

confidence: 99%

Molecularly Imprinted Polymers with Strong Carboxypeptidase A‐Like Activity: Combination of an Amidinium Function with a Zinc‐Ion Binding Site in Transition‐State Imprinted Cavities

2004

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Section: Methodsmentioning

confidence: 99%

Molecularly Imprinted Polymers with Strong Carboxypeptidase A‐Like Activity: Combination of an Amidinium Function with a Zinc‐Ion Binding Site in Transition‐State Imprinted Cavities

2004

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“…Nonetheless, a mechanistic analysis of selected catalytic antibodies established that, as scheduled, they promoted the disfavored B Ac 2 mechanism by some 6-7 decades relative to the uncatalyzed reaction rate. DF8D5 thus emerged as one of the most effective catalytic antibodies generated in the mid-1990s [10]. However, its performance (as IgG or Fab) was still two slow for in vivo development, and the general K m of such abzymes for the prodrug was on the high side for potential therapeutic use.…”

confidence: 99%

Passive and catalytic antibodies and drug delivery

Blackburn

Rickard

Cesaro-Tadic

et al. 2004

Pure and Applied Chemistry

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Antibodies are one of the most promising components of the biotechnology repertoire for the purpose of drug delivery. On the one hand, they are proven agents for cell-selective delivery of highly toxic agents in a small but expanding number of cases. This technology calls for the covalent attachment of the cytotoxin to a tumor-specific antibody by a linkage that is reversible under appropriate conditions (antibody conjugate therapy, ACT-"passive delivery"). On the other hand, the linker cleavage can be accomplished by a protein catalyst attached to the tumor-specific antibody ("catalytic delivery"). Where the catalyst is an enzyme, this approach is known as antibody-directed enzyme prodrug therapy (ADEPT). Where the transformation is brought about by a catalytic antibody, it has been termed antibody-directed abzyme prodrug therapy (ADAPT). These approaches will be illustrated with emphasis on how their demand for new biotechnology is being realized by structure-based protein engineering.

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“…It proceeds by a stepwise mechanism in which the rate-limiting step is the formation of the tetrahedral intermediate. 19 However , the simultaneous bond breakage and bond formation of the carbonyl carbon in T ± concerted , Scheme 1, pathway (b) breaks only slightly (if at all) in the transition state. 20 Since the effects of substituent more or less cancel, small ρ values for concerted mechanisms were reported.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Aminolysis of N,N-Diethyl Carbamic Ester of HOBt Derivatives

Khattab¹,

Hassan²,

Hamed³

et al. 2010

Bulletin of the Korean Chemical Society

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The reaction of N,N-diethyl carbamates of 1H- [1,2,3]triazolo [4,5-b]pyridin-1-ol (4-HOAt) 7, 3H-[1,2,3]triazolo [4,5-b] and 6-nitro-1H-benzo[d][1,2,3]triazol-1-ol (NO2-HOBt) 12 with morpholine and piperidine in CH3CN underwent acyl nucleophilic substitution to give the corresponding carboxamide derivatives. The reactants and products were identified by elemental analysis, IR and NMR. We measured the kinetics of these reactions spectrophotometrically in CH3CN at a range of temperatures. The rates of morpholinolysis and piperidinolysis were found to fit the Hammett equation and correlated with σ-Hammett values. The values were 1.44 -1.21 for morpholinolysis and 1.95 -1.72 for piperidinolysis depending on the temperature. The Brønsted-type plot was linear with a βlg = −0.49 ± 0.02 and −0.67 ± 0.03. The kinetic data and structure-reactivity relationships indicate that the reaction of 9-12 with amines proceeds by a concerted mechanism. The deviation from linearity of the correlation ∆H # vs. ∆S # and plot of logkpip vs. logkmorph and Brønsted-type correlation indicate that the reactions of amines with carbamates 7 and 8 is attributed to the electronic nature of their leaving groups.

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Antibody Catalysis of B_Ac2 Aryl Carbamate Ester Hydrolysis: A Highly Disfavored Chemical Process. J. Am. Chem. Soc. 1997, 119, 2315−2316

Cited by 7 publications

References 0 publications

Molecularly Imprinted Polymers with Strong Carboxypeptidase A‐Like Activity: Combination of an Amidinium Function with a Zinc‐Ion Binding Site in Transition‐State Imprinted Cavities

Molecularly Imprinted Polymers with Strong Carboxypeptidase A‐Like Activity: Combination of an Amidinium Function with a Zinc‐Ion Binding Site in Transition‐State Imprinted Cavities

Passive and catalytic antibodies and drug delivery

Synthesis and Aminolysis of N,N-Diethyl Carbamic Ester of HOBt Derivatives

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