Ciba Foundation Symposium - Biosynthesis of Terpenes and Sterols

325 Pages·1959·5.721 MB·English

BIOSYNTHESIS OF
TERPENES AND STEROLS
Ciba Foundation Symposia
General Volumes :
Mammalian Germ Cells - - - - -
Preservation and Transplantation of Normal
Tissues - - - - - -
LeukaemiaResearch - - - -
Chemistry and Biology of Pteridines -
Porphyrin Biosynthesis and Metabolism
Histamine - - - - - -
Extrasensory Perception - - -
Bone Structure and Metabolism - -
Paper Electrophoresis - - - -
Ionizing Radiations and Cell Metabolism
TheNatureofViruses - - - -
-
Chemistry and Biology of Purines -
Drug Resistance in Micro-organisms -
Chemistry and Biology of Mucopolysaccharides
The CerebrospinalFluid - - - -
Neurological Basis of Behaviour - - -
AmAicntoiv Aityc ids a-n d Pe-p tide-s wit-h An-ti met-ab olic-
Medical Biology and Etruscan Origins - -
A leajet giving fuller details of these volumes, also of the Ciba
Foundatiora Colloquia m Endorrinohgy and Colloquia on
Ageing, is available from the Publishers
CIBA FOUNDATION SYMPOSIUM
ON THE
BIOSYNTHESIS OF
TERPENES AND STEROLS
Editors for the Ciba Foundation
G. E. W. WOLSTENHOLME, O.B.E., M.A., M.B., B.Ch.
and
MAEVE O’CONNOR, B.A.
With 102 nlustrations
LITTLE, BROWN AND COMPANY
BOSTON
ALL RIGHTRS ESERVED
This book may not be reproduced by
any means, in whle or in part, with-
out the permission of the Publishers
Published in London by
J. & A. Churchill Ltd.
104 Gloucester Place, W.l
First published 1959
Printed in Great Britain
THE Ciba Foundation, a unique international institution,
owes its inception to the generosity of CIBA Limited, Basle.
However, being established under British trust law, it enjoys
complete independence in practice and policy.
Under the guidance of its distinguished Trustees, the
Foundation offers accommodation to scientists from all over
the world at its home in Portland Place. Foremost in its acti-
vities is the organization of small conferences, the proceedings
of which are published in book form in the manner of the
present volume. The Foundation convenes many other in-
formal discussions between research workers of different dis-
ciplines and different nationalities and each year invites an
outstanding authority to deliver a special lecture. An exchange
programme between French and British postgraduates is con-
ducted and a library service is available. Furthermore, the
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is symbolized in the armorial bearings by five interlaced rings
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and the crozier, symbols associated with Basle, refer to the
sponsoring firm located in this ancient Swiss town.
V
THE CIBA FOUNDATION
for the Promotion of International Co-opmation in Medical and Chemical Research
41 PORTLANPUDC E, LONDONW, .1.
Trustees
THE RIGHTH ON.L ORDA DRIAN,O .M., F.R.S.
THE RT. HON. LORDB EVERIDOEK,. C.B., F.B.A.
SIR RUSSELLB RAIN, BT.
THE HON.S IR GEORGEL LOYD-JACOB
SIR RAYMONNDE EDHAMQ,. C., F.S.A.
Ezecutive Council
SIR RAYMONNDE EDHAMC, hairman PROFESSDORR. D R. h.c. R. MEIER
LORDB EVERIDGE MR. PHILIPM AIR
PROFESSAO. RH ADDOWF.,R .S. PROFESSFO. RG . YOUNGF, .R.S.
Director, and Secretary lo the Ezewlive Council
DR. G. E. W. WOLSTENHOLMO.EB,. E.
Deputy Director
Da. H. N. H. GENESE
Assistant Secretay
MISS N. BWND
Editm*al Assistanls
MISS CECILIA M. O'CONNORB, .Sc. MISS MAEVEO 'CONNORB,. A.
Librarian
MISS JOAENT HERINGTON
PREFACE
THE suggestion that there should be a Ciba Foundation
symposium on the biosynthesis of sterols had been put forward
whenever opportunity offered over several years by Professor
K. Bloch, Dr. G. PopjSk and Professor S. Bergstrom. A
further stimulus occurred when Dr. K. Folkers and his group
published their work on the synthesis of mevalonic acid. When
such a meeting could be fitted into the Foundation’s pro-
gramme of conferences, Sir Robert Robinson gave his support
by kindly agreeing to act as Chairman. Under his enthusi-
astic direction and with Dr. Popjitk’s continued assistance, the
proceedings finally took the form recorded here. Invaluable
advice on nomenclature was given by Dr. W. Klyne when the
book was being prepared for publication.
Experience has shown that these meetings are of the
greatest value when the number of those attending is strictly
limited. On this occasion thirty-seven members from seven
countries were present, but some six or eight of them attended
only one or two sessions of special interest to them. It is hoped
that this record will prove useful to those workers in the field
who could not be invited to participate, and also to those
whose work is concerned with wider or more general aspects of
such studies in biochemistry, physiology and pathology.
CONTENTS
PAGE
Chairman’s opening remarks
Sir ROBERRTO BINSON 1
Biogenesis and transformations of squalene
.
by K. BLOCH 4
Discussion : BIRCH,B LOCH,C OON, CORNFORTH, HORNING,
ISLERJE, GEPRO,P JAKR, OBINSON 16
Discovery and elucidation of mevalonic acid
by K. FOLKERCS., H. SHUNKB,. 0. LINN,F . M. ROBIN-
SON, P. E. WITTRE.IC HJ. ,W . HUFF,J . L. GILFILLANa nd
HELENR . SKEGGS 20
Discussion: BLOCHF,O LKERGSO, ODWIGNR, OB,I SLERK,L YNE,
.
KODICEKL,Y NENP, OPJAK,R OBINSON 4.3
Alterations of cholesterol biosynthesis in liver cell fractions
from rats in various experimental conditions
.
by NANCYL. R. BUCHER 46
Discussion: BUCHERD,A ENIKERL,Y NENP,O PJAR, SORM . 60
The enzymic synthesis of branched-chain acids
by M. J. COON, F. P. KWIECKIE, . E. DEKKERM, . J.
.
SCHLESINGaEnRd ALICE DEL CAMPILLO 62
Discussion : BL. OCH,C OON, LYNEN, POPJAK, ROBINSON,
RUDNEY 72
The biosynthesis of p-hydroxy-P-methyl-glutaryl co-
enzyme A and its conversion to mevalonic acid
.
~~H.RUDNEY 75
.
Discussion: COON, ISLERL,Y NENP,O PJAK, RUDNEY 91
New aspects of acetate incorporation into isoprenoid pre-
cursors
.
@F.LYNEN 95
Discussion :B LOCHF, OLKERGSR,O B, ISLERLY, NENP, OPJhK,
.
ROBINSON 116
Viii
CONTENTS ix
PAGE
The mechanism of a rearrangement occurring during
biosynthesis of cholesterol
by J. W. CORNFORTH,R ITAH . CORNFORTHM,. A RJORIE G..
HORNINGA., PELTERa nd G. POPJAK 119’
.
Discussion :B LOCHC,O RNFORTHR, OBINSON 132
Semi-, mono-, sesqui-, and triterpenes as cholesterol pre-
cursors
by 0.I SLERR,. RUEGGG, . SAUCYJ,. WURSCHK, . F. GEY.
and A. PLETSCHER 135
Discussion: ARI.G ONIB, IRCHI,S LEJRO,N ESL, YNENR,O BINSO. N,
RUDNEY 146
Biosynthesis of squalene and of cholesterol from mevalonic
acid
. .
by G. POPJAK 148
Discussion : BLOCHB, UCHERM, RS. CORN.F ORTH,G OSSELIN. ,
HORNINGLY, NEN,P OPJAK,R OBINSON 170
Biosynthesis of yeast sterols and the preparation of lrC-
labelled vitamin D, . .
by E. KODICEK 173
Discussion : BIR.C HB, LOCHC,O ON, GLOVER,K ODICEKL,Y NE.N ,
RUDNEY 183
Bile acids : formation and .m etabolism .
by S. BERGSTROM 185
Discussion :B ERGSTROBMI.R, CHB, LOCHB,O YDC, OON, GLOVE.R ,
HASLEWOOKDLY, NE 203
Species comparison as an aid in the study of the process
sterols + bile salts
. .
by G. A. D. HASLEWOOD 206
Discussion. : ARIGONI, BERGSTROMB, LOCH,H ASLEWO. OD,
JEGER 214
Some aspects of acid-catalysed cyclizations of terpenoid
polyenes
by A. ESCHENMOSDE.OR ,R OTHF~EEL IXM, . GUT, J. MEIER.
and P. STADLER 217
.
SORM
Discussion :B ARTONE,S CHENMOSREORB, INSON, 227
X CONTENTS
PAGE
Biogenesis of terpene.s in moulds and higher plants .
by D. ARIGONI 231
.
Discussion :A RIGONIB, ARTONJ,O NESP, OPJ~RKO, BINSON 243
The biosynthesis of terpenoid compo.u nds in fungi
.
by A. J. BIRCHa nd H. SMITH 245
Discussion: ARIGONI,B IRCH, BLO.C H,G OODWINJ, ONE.S ,
KLYNEL, YNENR, OBINSONSM, ITH 263
The biosynthesis of carotenoids by micro-organisms
. .
by E. C. GROB 267
.
Discussion: BLOCHC,O ON, GOODWING,R OBL, YNENP, OPJAK 277
A comparison of the incorporation of labelled GO,, acetate
and mevalonate into carotenoids in a number of caroteno-
genic systems .
.
by T. W. GOODWIN 279
Discussion : BLOCHC, OON,C OR.N FORTGHL, OVERG, OODW.I N,
LYNEN,P OPJAKR, UDNEY 291
General Discussion
BLOCH,B OYD, BUCHER,C ORNFORTHES, CHENMOSER,
GLOVER,H . ASLEWOODM, ORTON,P OPJAK, ROBINSO. N,
RUDNEY 295
Chairman's closing remarks .
.
SIRR OBERTR OBINSON 302