While we are at it, let's do the same thing for the second step of the mechanism. Again, what is happening with the arrows circled in red below? Cys157 Cys157 Cys157 His296 His296 His296 OH HO HO HN, HN, HN Co2 Asn329 Asn329- Asn329- Cys157 His296 он „OH HNNH Asn329 O deprotonation of the conjugate acid form of imidazole, followed by general base assistance in decarboxylation nucleophilic addition of the cysteine side chain to imidazole O decarboxylation coupled with the generation of molecular hydrogen (H2) O general acid catalyzed isomerization covalent attachment of the substrate to the enzyme

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter9: Alkynes: An Introduction To Organic Synthesis
Section9.SE: Something Extra
Problem 49AP: Occasionally, a chemist might need to invert the stereochemistry of an alkene—that is, to convert...
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While we are at it, let's do the same thing for the second step of the mechanism. Again, what is
happening with the arrows circled in red below?
Cys157
Cys157
Cys157
His296
His296
His296
OH
OH
HN,
HN
HN
-CO2
CH2
Asn329
Asn329
Asn329-
Cys157
His296
OH
OH
HNNH HyC.
H,C.
Asn329-
O deprotonation of the conjugate acid form of imidazole, followed by general base assistance in decarboxylation
O nucleophilic addition of the cysteine side chain to imidazole
O decarboxylation coupled with the generation of molecular hydrogen (H2)
O general acid catalyzed isomerization
n covalent attachment of the substrate to the enzyme
Transcribed Image Text:While we are at it, let's do the same thing for the second step of the mechanism. Again, what is happening with the arrows circled in red below? Cys157 Cys157 Cys157 His296 His296 His296 OH OH HN, HN HN -CO2 CH2 Asn329 Asn329 Asn329- Cys157 His296 OH OH HNNH HyC. H,C. Asn329- O deprotonation of the conjugate acid form of imidazole, followed by general base assistance in decarboxylation O nucleophilic addition of the cysteine side chain to imidazole O decarboxylation coupled with the generation of molecular hydrogen (H2) O general acid catalyzed isomerization n covalent attachment of the substrate to the enzyme
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