Introduction to Enzyme and Coenzyme Chemistry - E-Library Home

Enzymatic Carbon–Carbon Bond Formation 191
C.H. Wong & G.M. Whitesides (1994) Enzymes in Synthetic Organic Chemistry. Pergamon,
Oxford.
Claisen enzymes
S.I. Chang & G.G. Hammes (1990) Structure and mechanism of action of a multifunctional
enzyme: fatty acid synthase. Acc. Chem. Res., 23, 363–9.
J.D. Clark, S.J. O’Keefe & J.R. Knowles (1988) Malate synthase: proof of a stepwise
Claisen condensation using the double-isotope fractionation test. Biochemistry,
27, 5961–71.
J.S. Staunton (1991) The extraordinary enzymes involved in erythromycin biosynthesis.
Angew. Chem. Intl. Ed. Engl., 30, 1302–6.
Carboxylases
P.V. Attwood & J.C. Wallace (2002) Chemical and catalytic mechanisms of carboxyl
transfer reactions in biotin-dependent enzymes. Acc. Chem. Res., 35, 113–20.
P. Dowd, R. Hershline, S.W. Ham & S. Naganathan (1994) Mechanism of action of
vitamin K. Nat. Prod. Reports, 11, 251–64.
F.C. Hartman & M.R. Harpel (1994) Chemical and genetic probes of the active site of d-
ribulose-1,5-bisphosphate carboxylase-oxygenase: a retrospective based on the threedimensional
structure. Adv. Enzymol., 66, 1–76.
J.R. Knowles (1989) The mechanism of biotin-dependent enzymes. Annu. Rev. Biochem.,
58, 195–222.
N.F.B. Phillips, M.A. Shoswell, A. Chapman-Smith, D.B. Keech & J.C. Wallace (1992)
Isolation of a carboxyphosphate intermediate and the locus of acetyl CoA action in
the pyruvate carboxylase reaction. Biochemistry, 31, 9445–50.
J.W. Suttie (1985) Vitamin K-dependent carboxylase. Annu. Rev. Biochem.,
54, 459–78.
Thiamine pyrophosphate
F. Jordan (2003) Current mechanistic understanding of thiamin diphosphate-dependent
enzymatic reactions. Nat. Prod. Reports, 20, 184–201.
R. Kluger, J. Chin, & T. Smyth (1981) Thiamin-catalyzed decarboxylation of pyruvate.
Synthesis and reactivity analysis of the central, elusive intermediate, a-lactylthiamin.
J. Am. Chem. Soc., 103, 884–8.
Terpene cyclases
D.E. Cane (1990) Enzymatic formation of sesquiterpenes. Chem. Rev., 90, 1089–103.
R.B. Croteau, C.J. Wheeler, D.E. Cane, R. Ebert & H.J. Ha (1987) Isotopically sensitive
branching in the formation of cyclic monoterpenes: proof that ( )a-pinene and
( )b-pinene are synthesised by the same monoterpene cyclase via deprotonation of a
common intermediate. Biochemistry, 26, 5383–9.
C.A. Lesburg, G. Zhai, D.E. Cane, and D.W. Christianson (1997) Crystal structure of
pentalenene synthase: mechanistic insights on terpenoid cyclization reactions in
biology. Science, 277, 1820–24.
M. Seemann, G. Zhai, J.W. de Kraker, C.M. Paschall, D.W. Christianson & D.E. Cane
(2002) Pentalenene synthase. Analysis of active site residues by site-directed
mutagenesis. J. Am. Chem. Soc., 124, 7681–9.