Stereochemistry of hydroxylation during the conversion of α-ketoisocaproate to β-hydroxyisovalerate by 4-hydroxyphenylpyruvate dioxygenase

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 22, 1996, Pages 2721-2724

  Adlington, Robert M ^a   Baldwin, Jack E ^a   Crouch, Nicholas P ^a   Lee, Meng Huee ^a   MacKinnon, Colin H ^a   Paul, Diana R ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYPHENYLPYRUVATE DIOXYGENASE; HYDROXYACID; OXYGENASE;

ARTICLE; ENZYME ACTIVITY; HYDROXYLATION; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030593854     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(96)00489-1     Document Type: Article

References (6)

1. 1) Sabourin, P. J.; Bieber, L. L. J. Biol. Chem. 1982, 257, 7460 and references cited therein.
2. 2) Baldwin, J. E.; Crouch, N. P.; Fujishima, Y.; Lee, M.-H.; MacKinnon, C. H.; Pitt, J. P. N.; Willis, A. C. Bioorg. Med. Chem. Lett. 1995, 5, 1255.
3. 3) Baldwin, J. E.; Crouch, N. P.; Lee, M.-H.; MacKinnon, C. H.; Zhang, Z. H. Bioorg. Med. Chem. Lett. 1996, 6, 1503.
4. 4) Lindblad, B; Linstedt, S.; Olander, B. and Omfelt, M., Acta. Chem. Scand. 1971, 25, 329 and references cited therein.
5. 5) Han, H. and Pascal Jr, R. A. J. Org. Chem. 1990, 55, 5173.
6. 1H NMR spectroscopy. The methyl group showed a major resonance (ca. 90%) at δ 0.92 (d, J 6.5 Hz) and a minor one (10%) at δ 0.94 (d, J 6.5 Hz) in contrast to the two equal intensity doublets observed from the amide 13c. Likewise, ca 92% e.e. for 12b was established.