Sets of aldolase antibodies with antipodal reactivities. Formal synthesis of epothilone e by large-scale antibody-catalyzed resolution of thiazole aldol

Organic Letters

Volumn 1, Issue 10, 1999, Pages 1623-1626

  Sinha, Subhash C ^a   Sun, Jian ^a   Miller, Gregory ^a   Barbas III, Carlos F ^a   Lerner, Richard A ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC ANTIBODY; EPOTHILONE DERIVATIVE; EPOTHILONE E; EPOXIDE; FRUCTOSE BISPHOSPHATE ALDOLASE; MONOCLONAL ANTIBODY; THIAZOLE DERIVATIVE;

ARTICLE; CHEMISTRY; IMMUNIZATION; IMMUNOLOGY; SYNTHESIS;

ANTIBODIES, CATALYTIC; ANTIBODIES, MONOCLONAL; EPOTHILONES; EPOXY COMPOUNDS; FRUCTOSE-BISPHOSPHATE ALDOLASE; IMMUNIZATION; THIAZOLES;

EID: 0033581769     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990261h     Document Type: Article

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34. 3CN, 10 μL) and aldolase antibodies (6 μM solution in PBS, 90 μL) was kept at room temperature for 12 h and then analyzed by HPLC (ODR column, see Supporting Information). Reaction mixtures containing antibodies 84G3, 85H6, and 93F3 were found to possess only one enantiomer of (±)-8a.
35. 2BOTf and acetone) with the aldehyde 9a. (For HPLC conditions, see the Supporting Information.)
36. 3CN, 10 μL) were incubated with the antibody 84G3, 85H6, or 93G3 (90 μL of 6 μM antibody solution in PBS buffer, pH 7.4) and progress of the reaction was followed by HPLC equipped with a chiral reverse phase ODR column (Daicel Chemical Industries). (For HPLC conditions, see the Supporting Information.)
37. Antibodies recovered after one reaction cycle retained their catalytic activity.
38. +).
39. 3).