Literature DB >> 9843936

The antibody catalysis route to the total synthesis of epothilones.

S C Sinha1, C F Barbas, R A Lerner.   

Abstract

An efficient monoclonal aldolase antibody that proceeds by an enamine mechanism was generated by reactive immunization. Here, this catalyst has been used in the total synthesis of epothilones A (1) and C (3). The starting materials for the synthesis of these molecules have been obtained by using antibody-catalyzed aldol and retro-aldol reactions. These precursors were then converted to epothilones A (1) and C (3) to complete the total synthesis.

Entities:  

Mesh：

Substances：

Year:  1998        PMID： 9843936      PMCID： PMC24496          DOI： 10.1073/pnas.95.25.14603

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN： 0027-8424            Impact factor:   11.205


  20 in total

1.  Studies toward a Synthesis of Epothilone A: Use of Hydropyran Templates for the Management of Acyclic Stereochemical Relationships.

Authors:  Dongfang Meng; Erik J. Sorensen; Peter Bertinato; Samuel J. Danishefsky
Journal:  J Org Chem       Date:  1996-11-15       Impact factor: 4.354

2.  Immune versus natural selection: antibody aldolases with enzymic rates but broader scope.

Authors:  C F Barbas; A Heine; G Zhong; T Hoffmann; S Gramatikova; R Björnestedt; B List; J Anderson; E A Stura; I A Wilson; R A Lerner
Journal:  Science       Date:  1997-12-19       Impact factor: 47.728

3.  Asymmetric organic synthesis with catalytic antibodies.

Authors:  E Keinan; S C Sinha; D Shabat; H Itzhaky; J L Reymond
Journal:  Acta Chem Scand       Date:  1996-08

4.  Catalytic antibodies.

Authors:  A Tramontano; K D Janda; R A Lerner
Journal:  Science       Date:  1986-12-19       Impact factor: 47.728

5.  Selective chemical catalysis by an antibody.

Authors:  S J Pollack; J W Jacobs; P G Schultz
Journal:  Science       Date:  1986-12-19       Impact factor: 47.728

6.  Directed evolution of an esterase for the stereoselective resolution of a key intermediate in the synthesis of epothilones.

Authors:  U T Bornscheuer; J Altenbuchner; H H Meyer
Journal:  Biotechnol Bioeng       Date:  1998-06-05       Impact factor: 4.530

7.  Reactive immunization.

Authors:  P Wirsching; J A Ashley; C H Lo; K D Janda; R A Lerner
Journal:  Science       Date:  1995-12-15       Impact factor: 47.728

8.  Controlling chemical reactivity with antibodies.

Authors:  L C Hsieh; S Yonkovich; L Kochersperger; P G Schultz
Journal:  Science       Date:  1993-04-16       Impact factor: 47.728

9.  Epothilone B stabilizes microtubuli of macrophages like taxol without showing taxol-like endotoxin activity.

Authors:  P F Muhlradt; F Sasse
Journal:  Cancer Res       Date:  1997-08-15       Impact factor: 12.701

10.  Epothilone A induces apoptosis in neuroblastoma cells with multiple mechanisms of drug resistance.

Authors:  A Wolff; A Technau; G Brandner
Journal:  Int J Oncol       Date:  1997-07       Impact factor: 5.650
View more
  6 in total

1.  Multiple event activation of a generic prodrug trigger by antibody catalysis.

Authors:  D Shabat; C Rader; B List; R A Lerner; C F Barbas
Journal:  Proc Natl Acad Sci U S A       Date:  1999-06-08       Impact factor: 11.205

2.  Prodrugs of dynemicin analogs for selective chemotherapy mediated by an aldolase catalytic Ab.

Authors:  Subhash C Sinha; Lian-Sheng Li; Gregory P Miller; Shantanu Dutta; Christoph Rader; Richard A Lerner
Journal:  Proc Natl Acad Sci U S A       Date:  2004-02-23       Impact factor: 11.205

3.  Expanding the concept of chemically programmable antibodies to RNA aptamers: chemically programmed biotherapeutics.

Authors:  Ulrich Wuellner; Julia I Gavrilyuk; Carlos F Barbas
Journal:  Angew Chem Int Ed Engl       Date:  2010-08-09       Impact factor: 15.336

4.  Bringing biological solutions to chemical problems.

Authors:  P G Schultz
Journal:  Proc Natl Acad Sci U S A       Date:  1998-12-08       Impact factor: 11.205

5.  Expression and characterization of an enantioselective antigen-binding fragment directed against α-amino acids.

Authors:  Pierre P Eleniste; Heike Hofstetter; Oliver Hofstetter
Journal:  Protein Expr Purif       Date:  2013-07-01       Impact factor: 1.650

6.  Direct observation of an enamine intermediate in amine catalysis.

Authors:  Xueyong Zhu; Fujie Tanaka; Richard A Lerner; Carlos F Barbas; Ian A Wilson
Journal:  J Am Chem Soc       Date:  2009-12-30       Impact factor: 15.419
  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.