Amino Acids, Peptides and Proteins (SPR Amino Acids, Peptides, and Proteins (RSC)) (Vol 35)

454 Pages·2006·5.01 MB·English

by  John S. Davies

Amino Acids, Peptides and Proteins
Volume 35
A Specialist Periodical Report
Amino Acids, Peptides and Proteins
Volume 35
A Review of the Literature Published during 2002.
Editor
J.S. Davies, University of Wales, Swansea, UK
Authors
W.C. Chan, University of Nottingham, Nottingham, UK
D.T. Elmore, Oxfordshire, UK
E. Farkas, University of Debrecen, Debrecen, Hungary
A. Higton, Nottingham Trent University, Nottingham, UK
B. Penke, University Szeged, Hungary
I. So´va´go´, University of Debrecen, Debrecen, Hungary
G. To´th, University Szeged, Hungary
G. Va´radi, University Szeged, Hungary
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-10:0-85404-247-4
ISBN-13:978-0-85404-247-0
ISSN1361-5904
AcataloguerecordforthisbookisavailablefromtheBritishLibrary
rTheRoyalSocietyofChemistry2006
Allrightsreserved
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Preface
This35thVolumeintheserieshasnotappearedwithinatimeframethatwe
would all be proud of, but it is often difficult to recover from critical delays
broughtaboutmainlythroughpressureofwork.Howeveritisoursincerehope
that the hard work of our Chapter authors will form a real workhorse of a
sourcebook,representingtherelevantandimportantworkassociatedwiththe
period up to the end of 2002. With the expansion of the literature all our
Reporters have increasingly had to approach their task with a more selective
brief than was the case in earlier volumes of the series.
IntheabsenceofachapteronAminoAcidsinvolume34,Chapter1inthis
Volumecoversthetwo-yearperiod2001–2,andthistimealsowewelcomeback
the biennial Chapter on ‘Metal Complexes’ authored by Etelka Farkas and
ImreSo´va´go´ coveringthesameperiod.ColleaguesfromtheMedicalUniversity
of Szeged (Botond Penke, Ga´bor To´th and Gyo¨rgyi Va´radi) have continued
with their wide-ranging Chapter 3 reviewing Analogue and Conformational
StudiesonPeptides.ThecontinuinginvolvementofDonElmore,WengChan,
Avril Higton and John Davies from the UK has taken care of the other core
Chapters.SadlyduetofamilycommitmentsGrahamBarretthadtorelinquish
the role of Joint Senior Reporter, but we are grateful to Graham for his
contributions as an author within these Reports over many years. So the
currentvolumehasbeenco-ordinatedbyoneSeniorReporter,whoappreciates
verymuchthegenuineandunstintingeffortsofeveryonethathasbroughtthis
Volume to fruition. This includes the RSC personnel, who have patiently
waitedformanuscriptstoappearandensuredthateveryone’seffortshavebeen
transcribed to the document you are now reading.
Again to preserve good practice in presentation in peptide science, we are
grateful for the permission to reproduce John Jones’s most recent plea for
conformity of nomenclature in such a wide-ranging discipline. Over recent
volumes of these Reports we have reproduced his ‘Short Guide to Abbrevia-
tions’ published in 1999, but this time we have the opportunity of re-printing
themostrecentversionwhichappearedinJ.PeptideScience2006,11,pp.1–12.
During the production of this volume ‘Proceedings of the 18th American
Symposium at Boston’ in 2003 (eds. M. Chorev and T. K. Sawyer) appeared.
From the title of the book from these proceedings – Peptide Revolution:
Genomics, Proteomics andTherapeutics – comes ahint as towhere our subject
might be heading.
John S. Davies
UniversityofWales,Swansea
v

Contents
Cover
Thecrystalstructure
ofparticulatemethane
monooxygenase(pMMO)
revealsmanyunexpected
featuresincluding,atrimeric
oligomerizationstateandthree
distinctmetalcenters.Image
reproducedbypermissionof
AmyRosenzweigfromDalton
Transactions,2005.
Amino Acids 1
Weng C. Chan, Avril Higton and John S. Davies
1 Introduction 1
2 Reviews 1
3 Naturally-Occurring Amino Acids 2
3.1 New Naturally Occurring Amino Acids 2
4 Chemical Synthesis and Resolution of Amino Acids 2
4.1 General Methods for the Synthesis of a-Amino Acids,
including Enantioselective Synthesis 3
4.2 Synthesis of Protein Amino Acids and Other Naturally
Occurring Amino Acids 8
4.3 Synthesis of a-Alkyl a-Amino Acids 13
4.4 Synthesis of a-Amino Acids with Alicyclic and Long
Aliphatic Side Chains 14
4.5 Models for Prebiotic Synthesis of Amino
Acids 19
4.6 Synthesis of Halogenoalkyl a-Amino Acids 19
4.7 Synthesis of Hydroxyalkyl a-Amino Acids 20
4.8 Synthesis of N-Substituted a-Amino Acids 23
AminoAcids,PeptidesandProteins,Volume35
rTheRoyalSocietyofChemistry,2006
vii
viii AminoAcids,Pept.Proteins,2006,35,vii–xii
4.9 Synthesisofa-AminoAcidscarryingUnsaturatedAlipha-
tic Side Chains 24
4.10 Synthesisofa-AminoAcidswithAromaticorHeterocyc-
lic Side-Chains 27
4.11 Synthesis of a-Amino Acids carrying Amino Groups and
related Nitrogen Functional Groups in Aliphatic Side
Chains 32
4.12 Synthesis of a-Amino Acids with Side-Chains
carrying Boron Functional Groups 33
4.13 Synthesis of a-Amino Acids with Side Chains
carrying Silicon Functional Groups 33
4.14 Synthesis of a-Amino Acids with Side Chains
carrying Phosphorus Functional Groups 33
4.15 Synthesisofa-AminoAcidscarryingSulfurandSelenium
containing Side Chains 34
4.16 Synthesis of b-Amino Acids with Higher
Homologous Amino Acids 35
4.17 Resolution of DL-Amino Acids 38
5 Physico-Chemical Studies of Amino Acids 41
5.1 X-ray Crystal Analysis of Amino Acids and Their Deri-
vatives 41
5.2 Nuclear Magnetic Resonance Spectroscopy 41
5.3 Circular Dichroism 42
5.4 Mass Spectrometry 42
5.5 Other Spectroscopic Studies on Amino Acids 42
5.6 Measurements on Amino Acids in Solution 42
5.7 Measurements on Amino Acids in the Solid State 44
5.8 Amino Acids Adsorption and Transport
Phenomena 45
5.9 Host-Guest Studies with Amino Acids 46
5.10 Theoretical Calculations involving Amino Acids 48
6 Reactions and Analysis of Amino Acids 49
6.1 General and Specific Reactions of Amino Acids 49
6.2 Analysis of Amino Acids 50
References 50
Peptide Synthesis 74
Donald T Elmore
1 Introduction 74
2 Methods 74
2.1 Amino-group Protection 74
2.2 Carboxy-group Protection 76
2.3 Side-chain Protection 77
2.4 Disulfide Bond Formation 77
AminoAcids,Pept.Proteins,2006,35,vii–xii ix
2.5 Peptide Bond Formation 78
2.6 Peptide Synthesis on Macromolecular Supports and
Methods of Combinatorial Synthesis 83
2.7 Enzyme-mediated Synthesis and Semi-synthesis 88
2.8 Miscellaneous Reactions Related to Peptide
Synthesis 90
3 Appendix: A List of Syntheses in 2002 91
3.1 Natural Peptides, Proteins and Partial Sequences 91
3.2 Sequential Oligo- and Poly-peptides 95
3.3 Enzyme Substrates and Inhibitors 96
3.4 Conformations of Synthetic Peptides 97
3.5 Glycopeptides 99
3.6 Phosphopeptides and Related Compounds 101
3.7 Immunogenic and Immunosuppressant Peptides 101
3.8 Nucleopeptides, PNAs 101
3.9 Miscellaneous Peptides 102
3.10 Purification Methods 104
References 104
Analogue and Conformational Studies on Peptides,
Hormones and Other Biologically Active Peptides 129
Botond Penke, Ga´bor To´th and Gyo¨rgyi Va´radi
1 Introduction 129
2 Peptide Backbone Modifications and Peptide Mimetics 129
2.1 Aza,Oxazole,Oxazoline,Triazole,TriazineandTetrazole
Peptides 130
2.2 C[CHQCH], C[Z-CFQCH], C[CH(OH)–CH ],
2
C[CH(OH)–CH –NH], retro- and retro-inverso-
2
C[NHCH(CF )], C[CH O], retro-C[CONR], C[CO–
3 2
N(NPht)], C[O–CO–N], C[CO–NR–O], C[CH NH],
2
C[CO–CH -cyclopropyl-NH], C[PO R–N], C[PO R],
2 2 2
C[NHCO] 131
2.3 Rigid Amino Acid, Peptide and Turn Mimetics 136
3 Cyclic Peptides 152
4 Biologically Active Peptides 157
4.1 Peptides Involved in Alzheimer’s Disease 157
4.2 Antimicrobial Peptides 161
4.3 ACTH peptides 168
4.4 Angiotensin II Analogues and Non-peptide
Angiotensin II Receptor Ligands 168
4.5 Bombesin/Neuromedin Analogues 170
4.6 Bradykinin Analogues 171
4.7 Cholecystokinin Analogues, Growth
Hormone-Releasing Peptide and Analogues 173
x AminoAcids,Pept.Proteins,2006,35,vii–xii
4.8 Integrin-related Peptide and Non-Peptide
Analogues 174
4.9 LHRH and GnRH Analogues 186
4.10 a-MSH Analogues 186
4.11 MHC Class I and II Analogues 186
4.12 Neuropeptide Y (NPY) Analogues 187
4.13 Opioid (Neuropeptide FF, Enkephalin,
Nociceptin, Deltorphin and Dynorphin) Peptides 190
4.14 Somatostatin Analogues 193
4.15 Tachykinin (Substance P and Neurokinin)
Analogues 195
4.16 Vasopressin and Oxytocin Analogues 196
4.17 Insulins and Chemokines 197
4.18 Peptide Toxins 200
4.19 Miscellaneous 200
5 Enzyme Inhibitors 203
5.1 Aminopeptidase and Deformylase Inhibitors 203
5.2 Calpain Inhibitors 206
5.3 Carboxypeptidase Inhibitors 207
5.4 Caspase Inhibitors 208
5.5 Cathepsin and Other Cystein Protease Inhibitors 209
5.6 Cytomegalovirus and Rhinovirus 3C Protease Inhibitors 213
5.7 Converting Enzyme Inhibitors 214
5.8 Elastase Inhibitors 216
5.9 Farnesyltransferase Inhibitors 218
5.10 HIV-Protease Inhibitors 219
5.11 Matrix Metalloproteinase Inhibitors 223
5.12 NO-synthase Inhibitors 224
5.13 Proteasome Inhibitors 225
5.14 Protein Phosphatase Inhibitors 227
5.15 Renin and Other Aspartyl Proteinase Inhibitors 229
5.16 Thrombin and Factor-Xa Inhibitors 231
5.17 Trypsin and Other Serine Protease Inhibitors 233
5.18 tRNA Synthetase Inhibitors 235
5.19 Miscellaneous 236
6 Phage Library Leads 240
7 Protein-Protein Interaction Inhibitors 240
7.1 SH2 and SH3 Domain Ligands 240
8 Advances in Formulation/Delivery Technology 241
References 242
Cyclic, Modified and Conjugated Peptides 272
John S. Davies
1 Introduction 272