1998
DOI: 10.1021/ja973676b
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Aldolase Antibodies of Remarkable Scope

Abstract: This paper describes the substrate specificity, synthetic scope, and efficiency of aldolase catalytic antibodies 38C2 and 33F12. These antibodies use the enamine mechanism common to the natural Class I aldolase enzymes. Substrates for these catalysts, 23 donors and 16 acceptors, have been identified. The aldol acceptor specificity is expected to be much broader than that defined here since all aldehydes tested, with the exception polyhydroxylated aldehydes, were substrates for the antibodies. 38C2 and 33F12 ha… Show more

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Cited by 240 publications
(132 citation statements)
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“…Because cyclopentanone was found to be a very efficient donor in the 38C2-catalyzed aldol reaction (23), it was anticipated that prodrugs 11-12 could undergo the retro-aldol reaction faster than 9-10. The prodoxs 9-12 were synthesized by using dox hydrochloride and the aldol linkers, 25a-25b and 29a-29b, respectively (Scheme 1B).…”
Section: Resultsmentioning
confidence: 99%
“…Because cyclopentanone was found to be a very efficient donor in the 38C2-catalyzed aldol reaction (23), it was anticipated that prodrugs 11-12 could undergo the retro-aldol reaction faster than 9-10. The prodoxs 9-12 were synthesized by using dox hydrochloride and the aldol linkers, 25a-25b and 29a-29b, respectively (Scheme 1B).…”
Section: Resultsmentioning
confidence: 99%
“…Analogous to the strategy used by type I aldolases (10), formation of the iminium intermediate with the enzymatic lysine side chain provides an electron sink, facilitating the retroaldol cleavage. Several catalytic antibodies and peptide systems have been developed that utilize this lysine iminium strategy (11)(12)(13)(14)(15)(16).…”
mentioning
confidence: 99%
“…mAb 38C2 belongs to a group of catalytic antibodies that were generated by reactive immunization and mechanistically mimic natural aldolase enzymes (14,15). Through a reactive lysine, these antibodies catalyze aldol and retro-aldol reactions using the enamine mechanism of natural aldolases (14)(15)(16)(17)(18). In addition to their remarkable versatility and efficacy in synthetic organic chemistry (reviewed in ref.…”
mentioning
confidence: 99%