Amino Acids, Peptides and Proteins (SPR Amino Acids, Peptides, and Proteins (RSC)) (Vol 32)

379 Pages·2001·4.73 MB·English

by  J. S. Davies

A Spec ia Ii s t Periodi c a I Report
Amino Acids, Peptides and
Proteins
Volume 32
A Review of the Literature Published
during 1999
Senior Reporter
J. S. Davies, University of Wales, Swansea, UK
Reporters
G.C. Barrett, Oxford, UK
A. Dutta, formerlyAstraZeneca, Macclesfield, UK
D.T. Elmore, University of Oxford, UK
J.A. Littlechild, University of Exeter, UK
RSmC
ROYAL SOCIETY OF CHEMISTRY
ISBN 0-85404-232-6
ISSN 1361-5904
0T he Royal Society of Chemistry 2001
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Preface
Once again, the authors in this Volume of Reports, covering the year 1999,
have attempted as far as possible to comprehensively cover topics within
chapter titles that have long been recognised as pillars of the subject matter
under review. Within each chapter there are obviously evolutionary changes
over the years, as we now have to reflect that more and more publications are
all-encompassing in their subject content. Data on structure, synthesis, bio-
logical activity and analogue studies often appear in the same publication;
hence some overlap of publications between chapters has become inevitable.
Hopefully different viewpoints will have been highlighted as a result.
In last year’s volume, we referred to the need to be continually observant of
good standards in nomenclature and abbreviations. We understand that IUB-
IUPAC are reviewing this area, but while we await publication of their
deliberations, we are grateful to Dr. John Jones and to John Wiley & Sons Ltd
for permission to include in this volume the short guide on nomenclature and
abbreviations which originally appeared in J. Peptide Science, 1999, 5, 465.
This article has been reproduced unchanged from the original journal article.
Two major conferences in this research area have taken place while this
volume has been in gestation. The 16th American Peptide Symposium in
Minneapolis has given rise to Peptides for the New Millennium, eds. G.B.
Fields, J.P. Tam and G. Barany, Kluwer, Dordrecht, Netherlands, 2000,
829pp. The 26th European Peptide Symposium at Montpellier has given us
Peptides 2000, eds. Jean Martinez and Jean-Alain Fehrentz, Editions EDK,
Paris, 2001, 1055pp, which records the exciting developments presented there.
The contents of these books offer an overview of current developments, but
the policy adopted by all our Reporters is to allow the work contained in them
to mature into full papers before making comment.
This volume has again relied on a group of experienced Reporters, who have
laboured hard over many months. Graham Barrett, Donald Elmore, Anand
Dutta and Jennifer Littlechild all deserve sincere thanks for their compilations.
We understand that this year’s will be the last chapter we will receive from Anand
Dutta, who has over the years augmented our coverage by accessing a great deal
of pharmacological data on peptides, not freely available to many Reporters in
this series. We wish Anand well, as he takes on other fields of interest.
Finally the patience and professionalism of the RSC Publications staff have
again been instrumental in producing this volume of Reports, which we hope
will be a sourcebook and seedcorn for many future activities in this wide and
important field.
John S. Davies
University of Wales, Swansea
V
Contents
Chapter1 AminoAcids 1
ByGrahamC.Barrett
1 Introduction 1
2 TextbooksandReviews 1
3 NaturallyOccurringAminoAcids 2
3.1 OccurrenceofKnownAminoAcids 2
3.2 NewNaturallyOccurringAminoAcids 2
3.3 NewAminoAcidsfromHydrolysates 3
4 ChemicalSynthesisandResolutionofAminoAcids 5
4.1 GeneralMethodsfortheSynthesisofa-AminoAcids,
IncludingEnantioselectiveSynthesis 5
4.1.1 AminationofAlkanoicAcidDerivativesby
AminesandAmine-relatedReagents 5
4.1.2 CarboxylationofAlkylaminesandImines,and
RelatedMethods 8
4.1.3 UseofChiralSynthonsinAminoAcid
Synthesis 8
4.1.4 UseofRearrangementsGeneratinga
Carbon–NitrogenBond 11
4.1.5 OtherRearrangements 11
4.1.6 AmidocarbonylationandRelated
MulticomponentProcesses 11
4.1.7 FromGlycineDerivativesandfromIminesof
GlyoxylicAcidDerivatives 13
4.1.8 FromDehydro-aminoAcidDerivatives 17
4.2 SynthesisofProteinAminoAcidsandOther
Well-knownNaturallyOccurringAminoAcids 18
4.3 Synthesisofa-Alkyla-AminoAcids 21
4.4 Synthesisofa-AminoAcidsCarryingAlkyl
Side-chains,andCyclicAnalogues 22
4.5 ModelsforPrebioticSynthesisofAminoAcids 26
4.6 Synthesisofa-(o-Halogenoalkyl)-a-AminoAcids 26
AminoAcids,PeptidesandProteins,Volume32
#TheRoyalSocietyofChemistry,2001
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viii Contents
4.7 Synthesisofa-(o-Hydroxyalkyl)-a-AminoAcids 26
4.8 SynthesisofN-Substituteda-AminoAcids 27
4.9 Synthesisofa-AminoAcidsCarryingUnsaturated
AliphaticSide-chains 27
4.10 Synthesisofa-AminoAcidswithAromaticor
HeteroaromaticGroupingsinSide-chains 28
4.11 Synthesisofa-AminoAcidsCarryingAminoGroups,
andRelatedNitrogenFunctionalGroups,in
AliphaticSide-chains 29
4.12 Synthesisofa-AminoAcidsCarryingBoron
FunctionalGroupsinSide-chains 30
4.13 Synthesisofa-AminoAcidsCarryingSilicon
FunctionalGroupsinSide-chains 30
4.14 Synthesisofa-AminoAcidsCarryingPhosphorus
FunctionalGroupsinSide-chains 30
4.15 Synthesisofa-AminoAcidsCarryingSulfur-,
Selenium-orTellurium-containingSide-chains 30
4.16 Synthesisofb-AminoAcidsandHigherHomologous
AminoAcids 30
4.17 Resolutionofdl-AminoAcids 36
5 Physico-chemicalStudiesofAminoAcids 38
5.1 X-RayCrystalAnalysisofAminoAcidsandTheir
Derivatives 38
5.2 NuclearMagneticResonanceSpectrometry 39
5.3 OpticalRotatoryDispersionandCircular
Dichroism 39
5.4 MassSpectrometry 40
5.5 OtherSpectroscopicStudiesofAminoAcids 41
5.6 Physico-chemicalStudiesofAminoAcids 42
5.6.1 MeasurementsforAminoAcidSolutions 42
5.6.2 MeasurementsforSolidAminoAcids 43
5.6.3 AminoAcidAdsorptionandTransport
Phenomena 43
5.6.4 Host–GuestStudieswithAminoAcids 43
5.7 MolecularOrbitalCalculationsforAminoAcids 45
6 ChemicalStudiesofAminoAcids 45
6.1 Racemization 45
6.2 GeneralReactionsofAminoAcids 46
6.2.1 ThermalStabilityofAminoAcids 46
6.2.2 ReactionsattheAminoGroup 46
6.2.3 ReactionsattheCarboxyGroup 50
6.2.4 ReactionsatBothAminoandCarboxy
Groups 52
6.2.5 Reactionsatthea-CarbonAtomofa-and
b-AminoAcids 53
Contents ix
6.3 SpecificReactionsofAminoAcids 54
6.4 EffectsofElectromagneticRadiationonAmino
Acids 63
7 AnalyticalMethods 64
7.1 Introduction 64
7.2 Gas–LiquidChromatography 65
7.3 Ion-exchangeChromatography 65
7.4 Thin-layerChromatography 66
7.5 High-performanceLiquidChromatography 66
7.6 CapillaryZoneElectrophoresis(CZE),andRelated
AnalyticalMethods 68
7.7 AssaysforSpecificAminoAcids 69
8 References 70
Chapter2 PeptideSynthesis 107
ByDonaldT.Elmore
1 Introduction 107
2 Methods 107
2.1 Amino-groupProtection 107
2.2 Carboxyl-groupProtection 109
2.3 Side-chainProtection 110
2.4 DisulfideBondFormation 110
2.5 PeptideBondFormation 111
2.6 PeptideSynthesisonMacromolecularSupports 116
2.7 Enzyme-mediatedSynthesisandSemisynthesis 120
2.8 MiscellaneousReactionsRelatedtoPeptide
Synthesis 122
3 Appendix:AListofSynthesesReportedMainlyin1999 123
3.1 NaturalPeptides,ProteinsandPartialSequences 123
3.2 SequentialOligo-andPoly-peptides 128
3.3 EnzymeSubstratesandInhibitors 128
3.4 ConformationofSyntheticPeptides 130
3.5 Glycopeptides 131
3.6 PhosphopeptidesandRelatedCompounds 131
3.7 ImmunogenicandImmunosuppressantPeptides 131
3.8 Nucleopeptides 132
3.9 MiscellaneousPeptides 132
3.10 PurificationMethods 135
4 References 135
x Contents
Chapter3 AnalogueandConformationalStudiesonPeptides,Hormones
andOtherBiologicallyActivePeptides 163
ByAnandS.Dutta
1 Introduction 163
2 PeptideBackboneModificationsandDi-,Tri-Peptide
Mimetics 163
2.1 Aza,HydrazinoazaandAminoxyPeptides 163
2.2 c[CSNH],c[CH NH],c[PO CH ],
2 2 2
c[hydroxyethylene],c[dihydroxyethylene],
c[CH CH -N(isopropyl)-CO]andRetro-inverso
2 2
PeptideAnalogues 164
2.3 RigidAminoAcidDi-,Tri-peptideandTurn
Mimetics 165
3 CyclicPeptides 167
4 BiologicallyActivePeptides 170
4.1 PeptidesInvolvedinAlzheimer’sDisease 170
4.2 AntimicrobialPeptides 173
4.2.1 AntibacterialPeptides 173
4.2.2 AntifungalPeptides 177
4.3 ACTH/CRFPeptides 178
4.4 AngiotensinIIAnaloguesandNon-peptide
AngiotensinIIReceptorLigands 180
4.5 Bombesin/NeuromedinAnalogues 180
4.6 BradykininAnalogues 182
4.7 CholecystokininAnalogues 184
4.8 Complement-relatedPeptides 185
4.9 EndothelinAnalogues 187
4.10 GrowthHormone-releasingPeptideand
Non-peptideAnalogues 189
4.11 Integrin-relatedPeptideandNon-peptide
Analogues 191
4.11.1 IIb/IIIaAntagonists 191
4.11.2 a b Antoagonists 193
v 3
4.11.3 a b anda b Antagonists 195
4 1 5 1
4.12 LHRHAnalogues 195
4.13 a-MSHanalogues 196
4.14 MHCClassIandIIanalogues 198
4.15 NeuropeptideY(NPY)Analogues 201
4.16 Opioid(NeuropeptideFF,Enkephalin,Nociceptin
DeltorphinandDynorphin)Peptides 202
4.17 SomatostatinAnalogues 207
Contents xi
4.18 Tachykinin(SubstancePandNeurokinins)
Analogues 210
4.19 Thyrotropin-releasingHormoneAnalogues 211
4.20 VasopressinandOxytocinAnalogues 212
4.20.1 OxytocinPeptideandNon-peptide
Analogues 212
4.20.2 VasopressinPeptideandNon-peptide
Analogues 214
4.21 Miscellaneous(Insulin,ScavengerReceptor
Ligands,ChemokineReceptorAntagonists,
N-typeCalciumChannelBlockers,Urotensin
andCytotoxicPeptides) 215
5 EnzymeInhibitors 217
5.1 AminopeptidaseInhibitors 218
5.2 CalpainInhibitors 219
5.3 CaspaseInhibitors 219
5.4 CathepsinInhibitors 220
5.5 CytomegalovirusandRhinovirus3CProtease
Inhibitors 223
5.6 ConvertingEnzyme[Angiotensin(ACE),Neutral
Endopeptidase(NEP),Endothelin,TNF-a
ConvertaseandInterleukin-1b(ICE)]Inhibitors 225
5.6.1 AngiotensinConvertingEnzymeand
NeutralEndopeptidaseInhibitors 226
5.6.2 EndothelinConvertingEnzymeInhibitors 227
5.6.3 TNF-aConvertaseInhibitors 228
5.6.4 Interleukin1bConvertingEnzyme(IL-1b)
Inhibitors 228
5.7 ElastaseInhibitors 228
5.8 FarnesyltransferaseInhibitors 229
5.9 HIVProteaseInhibitors 231
5.10 MatrixMetalloproteinaseInhibitors 234
5.11 ProteinPhosphataseInhibitors(Ser/ThrorTyr) 238
5.12 ReninandOtherAspartylProteinaseInhibitors 239
5.13 ThrombinInhibitors(SerineProtease)and
ThrombinReceptorLigands 240
5.13.1 ThrombinInhibitors 240
5.13.2 ThrombinReceptorLigands 242
5.14 Miscellaneous[Aggrecanase,Carboxypeptidase,
Dipeptidyl-peptidase,ProlylEndopeptidase,Protein
TyrosineKinase,SerineProteasesIncluding
ChymaseandTryptase]Inhibitors 245
6 PhageLibraryLeads 249
xii Contents
7 Protein–ProteinInteractionInhibitors 250
7.1 SH2andSH3DomainLigands 250
8 AdvancesinFormulation/DeliveryTechnology 253
9 References 254
Chapter4 Cyclic,ModifiedandConjugatedPeptides 287
ByJ.S.Davies
1 Introduction 287
2 CyclicPeptides 287
2.1 GeneralConsiderations 287
2.2 CyclicDipeptides(Dioxopiperazines) 290
2.3 Cyclotripeptides 291
2.4 Cyclotetrapeptides 292
2.5 Cyclopentapeptides 293
2.6 Cyclohexapeptides 295
2.7 Cycloheptapeptides 297
2.8 Cyclooctapeptides/Cyclononapeptides 300
2.9 CyclodecapeptidesandHigherCyclicPeptides 300
2.10 PeptidesContainingThiazole/OxazoleRings 303
2.11 Cyclodepsipeptides 306
3 ModifiedandConjugatedPeptides 316
3.1 Phosphopeptides 316
3.2 GlycopeptideAntibiotics 317
3.3 Glycopeptides 321
3.3.1 O-Glyopeptides 324
3.3.2 N-Glycopeptides 324
3.3.3 C-LinkedandOtherLinkedGlycopeptides 325
3.4 Lipopeptides 327
4 MiscellaneousStructures 328
5 References 333
Chapter5 CurrentTrendsinProteinResearch 342
ByJenniferA.Littlechild
1 Introduction 342
2 ProteinFolding 342