Two complete syntheses of (S)-aspartate semi-aldehyde and demonstration that Δ²-tetrahydroisophthalic acid is a non-competitive inhibitor of dihydrodipicolinate synthase
Date
2004
Authors
Roberts, S.
Morris, J.
Dobson, R.
Baxter, C.
Gerrard, J.
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Journal article
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ARKIVOC, 2004; 10:166-177
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Sarah J. Roberts, Jonathan C. Morris, Renwick C.J. Dobson, Chris L. Baxter, and Juliet A. Gerrard
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Abstract
We report, in full, two 3-step syntheses of (S)-aspartate semi-aldehyde, an important synthetic and biosynthetic precursor, from diprotected aspartic acid. The first synthesis proceeds via a thioester, the second via a Weinreb amide. Each route yields pure (S)-aspartate semi-aldehyde in excellent yield. The utility of (S)-aspartate semi-aldehyde prepared in this manner was demonstrated with an inhibition study of dihydrodipicolinate synthase, wherein Δ2- tetrahydroisophthalic acid is shown to be a non-competitive inhibitor with respect to both substrates.
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