Amino Acids, Peptides and Proteins (SPR Amino Acids, Peptides, and Proteins (RSC))

350 Pages·2003·0.3 MB·English

by  J. S. Davies

Amino Acids, Peptides and Proteins
Volume 34
-
of charge
A Specialist Periodical Report
Amino Acids, Peptides and
Proteins
Volume 34
A Review of the Literature Published
during 2001
Senior Reporters
G.C. Barrett, Oxford, UK
J.S. Davies, University of Wales, Swansea, UK
Reporters
D.T. Elmore, Oxfordshire, UK
B. Penke, University Szeged, Hungary
G. Toth, University Szeged, Hungary
G. Varadi, University Szeged, Hungary
RSeC
advancing the chemical sciences
NEW FROM 2003
If you buy this title on standing order, you will be given FREE access to
the chapters online. Please contact [email protected] with proof of purchase to
arrange access to be set up.
Thank you.
ISBN 0-85404-242-3
ISSN 1361-5904
A catalogue record for this book is available from the British Library
0T he Royal Society of Chemistry 2003
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Preface
The literature on amino acids, peptides and proteins arrives in a variety of ways
at the desktops of those maintaining current awareness of these topic areas.
Whether our readers choose to read the online version of the chapters in this
volume or have the traditional book format in front of them, we offer this latest
volume on the 2001 literature, with the hope that new leads and further clarity
will be conveyed through browsing these chapters. During the production of this
volume, proceedings',2 of two major international symposia were published,
reflecting the wealth and spread of work currently being researched in this area.
We wait with interest for the contents of these proceedings to work their way to
edited journal presentations for further review.
The policy for Specialist Periodical Reports published by the Royal Society of
Chemistry continues to require in-depth and critical coverage of the literature.
The endeavours of the team of authors are focussed by this policy on to major
trends in current research. Although an approach to comprehensive coverage of
narrow topics can be seen here and there, in this volume the subject areas are
now vast and have called for compression and selectivity, particularly in the
proteins area.
For this volume we welcome new authors for a wide ranging chapter on
analogue and conformational studies on peptides and peptide hormones, now
under the authorship of Botond Penke, Gabor Toth and Gyorgyi Varadi from
the Medical University of Szeged, Hungary. We offer a warm welcome to them
and look forward to having their company in future volumes. Authors that have
been involved with previous volumes in this series have penned the other
chapters. So we are very grateful for the unstinting efforts of Donald Elmore,
Graham Barrett and John Davies, and for their commitment to the continuation
of this series of reports. Unfortunately the usual chapter on amino acids failed to
make the deadline for publication, but will appear in the next volume as a 2-year
compilation.
In order to preserve good practice in the use of abbreviations in peptide
science, we once again reproduce by permission from J. Wiley and Sons the
publishers, John Jones's 'Short Guide to Abbreviations' as published in J.
Peptide Science, 1999,5,465-471.
'
Peptides 2002 Proceedings of the 27th European Peptide Symposium, Sorrento, Italy. Eds. E.
Benedetti and C. Pedone, Edizioni Ziino, S.a.s, 2002, 1057pp.
Peptides: The wave of the Future. Proceedings of the 2nd International and 27th American Peptide
Symposium, San Diego, USA. Eds. M. Lebl and R.A. Houghten, American Peptide Symposium,
2001, llllpp.
V
vi Preface
As always, the reporters are sincerely grateful to RSC personnel who have
overseen the project, and who have ensured that their manuscripts are tran-
scribed efficiently to the document you are now reading.
Graham Barrett John Davies
Oxford Swansea
Contents
Chapter1 PeptideSynthesis 1
ByDonaldT.Elmore
1 Introduction 1
2 Methods 1
2.1 Amino-groupProtection 1
2.2 Carboxy-groupProtection 3
2.3 Side-chainProtection 4
2.4 DisulfideBondFormation 5
2.5 PeptideBondFormation 6
2.6 PeptideSynthesisonMacromolecularSupports
andMethodsofCombinatorialSynthesis 10
2.7 Enzyme-mediatedSynthesisandSemisynthesis 13
2.8 MiscellaneousReactionsRelatedtoPeptide
Synthesis 16
3 Appendix:AListofSynthesesin2001 18
3.1 NaturalPeptides,ProteinsandPartialSequences 19
3.2 SequentialOligo-andPoly-peptides 23
3.3 EnzymeSubstratesandInhibitors 23
3.4 ConformationsofSyntheticPeptides 25
3.5 Glycopeptides 26
3.6 PhosphopeptidesandRelatedCompounds 27
3.7 ImmunogenicPeptides 27
3.8 Nucleopeptides 28
3.9 MiscellaneousPeptides 29
3.10 PurificationMethods 31
References 31
AminoAcids,PeptidesandProteins,Volume34
”TheRoyalSocietyofChemistry,2003
vii
viii Contents
Chapter2 AnalogueandConformationalStudiesonPeptides,Hormones
andOtherBiologicallyActivePeptides 55
ByBotondPenke,Ga´borTo´thandGyo¨rgyiVa´radi
1 Introduction 55
2 PeptideBackboneModificationsandPeptideMimetics 55
2.1 Aza,Oxazole,OxazolidineandTetrazolePeptides 55
2.2 y[CHCH ],y[Z-CF(cid:1)CH],retro-y[NHCH(CF)],
2 2 3
y[epoxy],y[CONHNR],y[CSNH],y[oxetane],y
[CHNH]y[CHOH-cyclopropyl-CONH],
2
y[PORCH] 56
2
2.3 RigidAminoAcid,PeptideandTurnMimetics 57
3 CyclicPeptides 62
4 BiologicallyActivePeptides 65
4.1 PeptidesInvolvedinAlzheimer’sDisease 65
4.2 AntimicrobialPeptides 68
4.3 ACTHPeptides 74
4.4 AngiotensinIIAnaloguesandNon-peptide
AngiotensinIIReceptorLigands 74
4.5 Bombesin/NeuromedinAnalogues 74
4.6 BradykininAnalogues 75
4.7 CholecystokininAnalogues,GrowthHormone-
releasingPeptideandAnalogues 77
4.8 Integrin-relatedPeptideandNon-peptideAnalogues 78
4.9 LHRHandGnRHAnalogues 82
4.10 a-MSHAnalogues 83
4.11 MHCClassIandIIAnalogues 83
4.12 NeuropeptideY(NPY)Analogues 85
4.13 Opioid(NeuropeptideFF,Enkephalin,Nociceptin,
DeltorphinandDynorphin)Peptides 85
4.14 SomatostatinAnalogues 89
4.15 Tachykinin(SubstancePandNeurokinins)
Analogues 90
4.16 VasopressinandOxytocinAnalogues 92
4.17 InsulinandChemokines 93
4.18 PeptideToxins 93
4.19 Miscellaneous 95
5 EnzymeInhibitors 97
5.1 AminopeptidaseandDeformylaseInhibitors 97
5.2 CalpainInhibitors 98
5.3 CarboxypeptidaseInhibitors 99
5.4 CaspaseInhibitors 100
Contents ix
5.5 CathepsinandOtherCysteineProteaseInhibitors 101
5.6 CytomegalovirusandRhinovirus3CProtease
Inhibitors 102
5.7 ConvertingEnzymesandTheirInhibitors 103
5.8 ElastaseInhibitors 103
5.9 FarnesyltransferaseInhibitors 105
5.10 HIV-ProteaseInhibitors 107
5.11 MatrixMetalloproteinaseInhibitors 110
5.12 NO-SynthaseInhibitors 113
5.13 ProteasomeInhibitors 114
5.14 ProteinPhosphataseInhibitors 116
5.15 ReninandOtherAspartylProteinaseInhibitors 117
5.16 ThrombinandFactor-XaInhibitors 120
5.17 TyrpsinandOtherSerineProteaseInhibitors 122
5.18 tRNASynthetaseInhibitors 123
5.19 Miscellaneous 123
6 PhageLibraryLeads 125
7 Protein—ProteinInteractionInhibitors 126
7.1 SH2andSH3DomainLigands 126
8 AdvancesinFormulation/DeliveryTechnology 127
References 128
Chapter3 Cyclic,ModifiedandConjugatedPeptides 149
ByJohnS.Davies
1 Introduction 149
2 CyclicPeptides 150
2.1 GeneralConsiderations 150
2.2 CyclicDipeptides(IncludingDioxopiperazines) 153
2.3 Cyclotripeptides 158
2.4 Cyclotetrapeptides 158
2.5 Cyclopentapeptides 160
2.6 Cyclohexapeptides 163
2.7 Cycloheptapeptides 166
2.8 Cyclooctapeptides/Cyclononapeptides 167
2.9 CyclodecapeptidesandHigherCyclicPeptides 169
2.10 PeptidesContainingThiazole/OxazoleRings 172
2.11 Cyclodepsipeptides 178
3 ModifiedandConjugatedPeptides 188
3.1 Phosphopeptides 188