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Its due to the stability of the amide (more stable) compared with the
ester. The C-N bond has partial double bond character and is planar
compared with the single bond of an ester where only the C=O is planar.
Regards
joel
Mark Matthewson wrote:
Hi folks,
I was puzzled as I went through the literature and could not find out
why many esterases cannot catalyze the cleavage of an amide bond,
while proteases can hydrolyze esters. Is there a structural basis why
an esterase cannot hydrolyze an amide or peptide?
Would greatly appreciate your expertise and help.
Best regards,
Rick
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Joel Tyndall, PhD
Lecturer
National School of Pharmacy
University of Otago
PO Box 913 Dunedin 9054
New Zealand
Pukenga
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Te Whare Wananga o Otago
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Aotearoa
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