Threonine Serine-threonine PLP dehydratase Isoleucine NH3 || || CH3- CH,-C-coo- CH,-C-coo- a- Ketobutyrate OH Pyruvate CH,-CH-TPP OValine Leucine Isoleucine Valine Leucine A FIGURE 18.20 Biosynthesis of isoleucine, leucine, and valine. After the serine-threonine dehydratase reaction, one set of enzymes catalyzes the comparable reactions in valine and isoleucine synthesis. In bacteria, each end product regulates its own synthesis by inhibiting a specific enzyme.

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Propose a mechanism for the TPP-dependent step in isoleucine biosynthesis (see Figure). Draw the predicted product of this reaction.

Threonine
Serine-threonine PLP
dehydratase
Isoleucine
NH3
||
||
CH3- CH,-C-coo-
CH,-C-coo-
a- Ketobutyrate
OH
Pyruvate
CH,-CH-TPP
OValine
Leucine
Isoleucine
Valine
Leucine
A FIGURE 18.20 Biosynthesis of isoleucine, leucine, and valine. After the
serine-threonine dehydratase reaction, one set of enzymes catalyzes the
comparable reactions in valine and isoleucine synthesis. In bacteria, each
end product regulates its own synthesis by inhibiting a specific enzyme.
Transcribed Image Text:Threonine Serine-threonine PLP dehydratase Isoleucine NH3 || || CH3- CH,-C-coo- CH,-C-coo- a- Ketobutyrate OH Pyruvate CH,-CH-TPP OValine Leucine Isoleucine Valine Leucine A FIGURE 18.20 Biosynthesis of isoleucine, leucine, and valine. After the serine-threonine dehydratase reaction, one set of enzymes catalyzes the comparable reactions in valine and isoleucine synthesis. In bacteria, each end product regulates its own synthesis by inhibiting a specific enzyme.
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