Introduction to Enzyme and Coenzyme Chemistry - E-Library Home

190 Chapter 7
(9) Usnic acid is a natural product thought to be biosynthesised from two
molecules of an aromatic precursor. Suggest a biosynthetic pathway to
the aromatic precursor from acetyl CoA, and a mechanism for the conversion
to usnic acid.
O
O
Acetyl CoA
HO
OH
HO
O
OH
H 3 C
derived from
S-adenosyl methionine
OH
H 3 C
H 3 C
OH O
O
usnic acid
Further reading
General
R.H. Abeles, P.A. Frey & W.P. Jencks (1992) Biochemistry. Jones & Bartlett, Boston.
J. Mann (1987) Secondary Metabolism, 2nd edn. Clarendon Press, Oxford.
J.S. Staunton (1978) Primary Metabolism: A Mechanistic Approach. Clarendon Press,
Oxford.
C.T. Walsh (1979) Enzymatic Reaction Mechanisms. Freeman, San Francisco.
Aldolases
J.G. Belasco & J.R. Knowles (1983) Polarization of substrate carbonyl groups by yeast
aldolase: investigation by Fourier transform infrared spectroscopy. Biochemistry, 22,
122–9.
K.H. Choi, J. Shi, C.E. Hopkins, D.R. Tolan & K.N. Allen (2001) Snapshots of
catalysis: the structure of fructose-1,6-bisphosphate aldolase covalently bound to
the substrate dihydroxyacetone phosphate. Biochemistry, 40, 13868–75.
D.R. Hall, G.A. Leonard, C.D. Reed, C.I. Watt, A. Berry & W.N. Hunter (1999) The
crystal structure of Escherichia coli class II fructose-1,6-bisphosphate aldolase
in complex with phosphoglycolohydroxamate reveals details of mechanism and
speciWcity. J. Mol. Biol., 287, 383–94.
J.B. Jones (1986) Enzymes in organic synthesis. Tetrahedron, 42, 3341–403.
A.J. Morris & D.R. Tolan (1994) Lysine-146 of rabbit muscle aldolase is essential
for cleavage and condensation of the C3–C4 bond of fructose 1,6-bisphosphate.
Biochemistry, 33, 12291–7.
J. Sygusch, D. Beaudry & M. Allaire (1987) Molecular architecture of rabbit skeletal
muscle aldolase at 2.7 Å resolution. Proc. Natl. Acad. Sci. USA, 84, 7846–50.
E.J. Toone, E.S. Simon, M.D. Bednarski & G.M. Whitesides (1989) Enzyme-catalysed
synthesis of carbohydrates. Tetrahedron, 45, 5365–422.
G.M. Whitesides & C.H. Wong (1985) Enzymes as catalysts in synthetic organic chemistry.
Angew. Chem. Int. Ed. Engl., 24, 617–38.