Peptide Synthesis: Methods and Protocols

337 Pages·2020·10.476 MB·English

by  Waleed M. Hussein, Mariusz Skwarczynski, Istvan Toth

Methods in
Molecular Biology 2103
Waleed M. Hussein
Mariusz Skwarczynski
Istvan Toth Editors
Peptide
Synthesis
Methods and Protocols
M M B
ETHODS IN OLECULAR IO LO GY
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School of Lifeand MedicalSciences
University ofHertfordshire
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Peptide Synthesis
Methods and Protocols
Edited by
Waleed M. Hussein, Mariusz Skwarczynski, and Istvan Toth
School of Chemistry and Molecular Biosciences, The University of Queensland, St. Lucia, QLD, Australia
Editors
WaleedM.Hussein MariuszSkwarczynski
SchoolofChemistryandMolecular SchoolofChemistryandMolecularBiosciences
Biosciences TheUniversityofQueensland
TheUniversityofQueensland St.Lucia,QLD,Australia
St.Lucia,QLD,Australia
IstvanToth
SchoolofChemistryandMolecular
Biosciences
TheUniversityofQueensland
St.Lucia,QLD,Australia
ISSN1064-3745 ISSN1940-6029 (electronic)
MethodsinMolecularBiology
ISBN978-1-0716-0226-3 ISBN978-1-0716-0227-0 (eBook)
https://doi.org/10.1007/978-1-0716-0227-0
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Preface
Peptideshavemanyimportantbiologicalfunctions,andtheyhavebeenextensivelyusedas
drugsandvaccineantigens.Amajoradvantagetopeptidesisthattheyareeasilysynthesized
throughchemicalorbiologicalmethods.Solidandsolutionphasesyntheticmethodsusing
FmocorBocprotectinggroupscanbeemployedtoproducepeptides,usingeithermanual
or automated procedures, with or without microwave assistance. However, precision in
synthesis isof paramountimportance. Theappropriate selection of resins, linkers,and side
chain protecting groups is essential for successful synthesis. To facilitate this, for example,
protecting groups can be removed by a variety of techniques and conditions to optimize
productyieldandpurity.
To improve their drug-like properties, peptides can be coupled with lipids, sugars,
and/or nucleosides. Peptides can also be conjugated with other peptides, proteins, and
polymers for formulation or delivery purposes using a wide range of modern conjugation
andcondensationmethods.
In this book, a variety of procedures for synthetically producing peptides and their
derivatives are described. Techniques are presented in a practical, detailed, step-by-step
mannerin order to beeasily understandable and useful for skilledinvestigators and under-
graduate students alike. Troubleshooting sections, as well as details of alternative methods
thatcanbeusedtoaddressconceivablepotentialissues,areincludedasadditionalresources
withineachchapter.
The book provides an extensive collection of specific, thoroughly tested, scientifically
validtechniquesformanycrucialprocessesthatwillallowresearcherstoefficientlyprepare,
purify,characterize,andusepeptidesforchemical,biochemical,andbiologicalstudies.
St.Lucia,QLD,Australia WaleedM.Hussein
MariuszSkwarczynski
IstvanToth
v
Contents
Preface ..................................................................... v
Contributors................................................................. ix
1 SolutionPhasePeptideSynthesis:TheCaseofBiphalin...................... 1
DagmaraTymeckaandAleksandraMisicka
2 ApplicationofFmoc-SPPS,Thiol-MaleimideConjugation,and
Copper(I)-CatalyzedAlkyne-AzideCycloaddition“Click”Reaction
intheSynthesisofaComplexPeptide-BasedVaccine
CandidateAgainstGroupAStreptococcus .................................. 13
ChuankaiDai,RachelJ.Stephenson,MariuszSkwarczynski,
andIstvanToth
3 InSituNeutralizationProtocolsforBoc-SPPS ............................. 29
RamkrishnaAdhikaryandPhilipE.Dawson
4 AnhydrousHydrogenFluorideCleavageinBocSolidPhase
PeptideSynthesis ....................................................... 41
KirtikumarB.Jadhav,KatrinaJ.Woolcock,
andMarkusMuttenthaler
5 AutomatedSolid-PhasePeptideSynthesis.................................. 59
DirkF.H.Winkler
6 NewDevelopmentsinMicrowave-AssistedSolidPhase
PeptideSynthesis ....................................................... 95
SandeepK.SinghandJonathanM.Collins
7 ProtectingGroupsinPeptideSynthesis.................................... 111
MartinConda-SheridanandMaddeboinaKrishnaiah
8 SynthesisofO-AcylIsopeptides:StepwiseandConvergent
Solid-PhaseSynthesis.................................................... 129
TakuYoshiya
9 AnIsodipeptideBuildingBlockforMicrowave-Assisted
Solid-PhaseSynthesisofDifficultSequence-ContainingPeptides ............. 139
WaleedM.Hussein,MariuszSkwarczynski,andIstvanToth
10 SPOTSynthesis:TheSolid-PhasePeptideSynthesisonPlanarSurfaces........ 151
DirkF.H.Winkler
11 Solid-PhaseSynthesisofWollamideCyclohexapeptideAnalogs............... 175
AllanM.PriorandDianqingSun
12 SynthesisofBranchedPeptidesviaaSide-ChainBenzylEster ................ 189
JunjieLiu,JianLi,XiaoboTian,FengTang,andWeiHuang
13 Solid-PhaseSynthesisofOctapeptinLipopeptides .......................... 199
KarlA.Hansford,ZytaM.Ziora,MatthewA.Cooper,
andMarkA.T.Blaskovich
vii
viii Contents
14 PeptidomimeticSynthesis:DrugDiscoveryforAlzheimer’sDisease........... 215
YoshioHamadaandZytaM.Ziora
15 SynthesisofAmideBackbone-ModifiedPeptides ........................... 225
Abu-BakerM.Abdel-Aal,RichardRaz,GeorgePapageorgiou,
andJohnOffer
16 SynthesisofNickFects,aNewFamilyofCPPs,bySolid-Phase
PeptideSynthesis ....................................................... 239
€
Piret ArukuuskandUloLangel
17 ChemoenzymaticSynthesisofHIV-1GlycopeptideAntigens ................ 249
GuanghuiZong,ChaoLi,andLai-XiWang
18 SynthesisofAntimicrobialLipopeptidesUsingthe“CLipPA”
Thiol-EneReaction ..................................................... 263
YannO.Hermant,AlanJ.Cameron,PaulW.R.Harris,
andMargaretA.Brimble
19 DecarboxylativeCouplingsforLate-StagePeptideModifications ............. 275
MengYaoZhangandLaraR.Malins
20 PeptideandPseudopeptideBondSynthesisinPhosphorus
DipeptideAnalogs ...................................................... 287
ArturMuchaandPawełKafarski
21 MicrobioreactorTechniquesfor theProductionandSpectroscopic
CharacterizationofMicrobialPeptides .................................... 303
ZeinabG.Khalil,AngelaA.Salim,andRobertJ.Capon
22 Metal–PeptideComplexestoStudyNeurodegenerativeDiseases ............. 323
MariuszMital,JakubP.Se˛k,andZytaM.Ziora
Index ...................................................................... 337
Contributors
ABU-BAKERM.ABDEL-AAL • TheFrancisCrickInstitute,London,UK
RAMKRISHNAADHIKARY • DepartmentofChemistry,TheScrippsResearchInstitute,LaJolla,
CA,USA
PIRETARUKUUSK • InstituteofTechnology,TartuUniversity,Tartu,Estonia
MARKA.T.BLASKOVICH • InstituteforMolecularBioscience,TheUniversityofQueensland,
StLucia,QLD,Australia
MARGARETA.BRIMBLE • SchoolofChemicalSciences,TheUniversityofAuckland,Auckland,
NewZealand;TheMauriceWilkinsCentreforMolecularBiodiscovery,TheUniversityof
Auckland,Auckland,NewZealand;SchoolofBiologicalSciences,TheUniversityof
Auckland,Auckland,NewZealand
ALANJ.CAMERON • SchoolofChemicalSciences,TheUniversityofAuckland,Auckland,New
Zealand;TheMauriceWilkinsCentreforMolecularBiodiscovery,TheUniversityof
Auckland,Auckland,NewZealand;SchoolofBiologicalSciences,TheUniversityof
Auckland,Auckland,NewZealand
ROBERTJ.CAPON • InstituteforMolecularBioscience,UniversityofQueensland,Brisbane,
QLD,Australia
JONATHANM.COLLINS • CEMCorporation,Matthews,NC,USA
MARTINCONDA-SHERIDAN • DepartmentofPharmaceuticalSciences,CollegeofPharmacy,
UniversityofNebraskaMedicalCenter,Omaha,NE,USA
MATTHEWA.COOPER • InstituteforMolecularBioscience,TheUniversityofQueensland,St
Lucia,QLD,Australia
CHUANKAIDAI • SchoolofChemistryandMolecularBiosciences,TheUniversityof
Queensland,St.Lucia,QLD,Australia
PHILIPE.DAWSON • DepartmentofChemistry,TheScrippsResearchInstitute,LaJolla,CA,
USA
YOSHIOHAMADA • FacultyofFrontiersofInnovativeResearchinScienceandTechnology,
KonanUniversity,Kobe,Japan
KARLA.HANSFORD • InstituteforMolecularBioscience,TheUniversityofQueensland,St
Lucia,QLD,Australia
PAULW.R.HARRIS • SchoolofChemicalSciences,TheUniversityofAuckland,Auckland,
NewZealand;TheMauriceWilkinsCentreforMolecularBiodiscovery,TheUniversityof
Auckland,Auckland,NewZealand;SchoolofBiologicalSciences,TheUniversityof
Auckland,Auckland,NewZealand
YANNO.HERMANT • SchoolofChemicalSciences,TheUniversityofAuckland,Auckland,
NewZealand;TheMauriceWilkinsCentreforMolecularBiodiscovery,TheUniversityof
Auckland,Auckland,NewZealand;SchoolofBiologicalSciences,TheUniversityof
Auckland,Auckland,NewZealand
WEIHUANG • CASKeyLaboratoryofReceptorResearch,CASCenter forExcellencein
MolecularCellScience,ShanghaiInstituteofMateriaMedica,ChineseAcademyof
Sciences,Shanghai,China;UniversityofChineseAcademyofSciences,Beijing,China
WALEED M.HUSSEIN • SchoolofChemistryandMolecularBiosciences,TheUniversityof
Queensland,St.Lucia,QLD,Australia
ix
x Contributors
KIRTIKUMARB.JADHAV • FacultyofChemistry,InstituteofBiologicalChemistry,University
ofVienna,Vienna,Austria
PAWEŁKAFARSKI • DepartmentofBioorganicChemistry,WrocławUniversityofScienceand
Technology,Wrocław,Poland
ZEINABG.KHALIL • InstituteforMolecularBioscience,UniversityofQueensland,Brisbane,
QLD,Australia
MADDEBOINAKRISHNAIAH • DepartmentofPharmaceuticalSciences,CollegeofPharmacy,
UniversityofNebraskaMedicalCenter,Omaha,NE,USA
€
ULOLANGEL • InstituteofTechnology,TartuUniversity,Tartu,Estonia;Departmentof
BiochemistryandBiophysics,StockholmUniversity,Stockholm,Sweden
CHAOLI • DepartmentofChemistryandBiochemistry,UniversityofMaryland,College
Park,MD,USA
JIANLI • CASKeyLaboratoryofReceptorResearch,CASCenterforExcellenceinMolecular
CellScience,ShanghaiInstituteofMateriaMedica,ChineseAcademyofSciences,
Shanghai,China;UniversityofChineseAcademyofSciences,Beijing,China
JUNJIE LIU • CASKeyLaboratoryofReceptorResearch,CASCenter forExcellencein
MolecularCellScience,ShanghaiInstituteofMateriaMedica,ChineseAcademyof
Sciences,Shanghai,China;DepartmentofChemistry,NanchangUniversity,Nanchang,P.
R.China
LARAR.MALINS • ResearchSchoolofChemistry,AustralianNationalUniversity,Canberra,
ACT,Australia
ALEKSANDRAMISICKA • FacultyofChemistry,UniversityofWarsaw,Pasteura,Warsaw,
Poland
MARIUSZMITAL • InstituteforMolecularBioscience,TheUniversityofQueensland,StLucia,
QLD,Australia
ARTURMUCHA • DepartmentofBioorganicChemistry,WrocławUniversityofScienceand
Technology,Wrocław,Poland
MARKUSMUTTENTHALER • FacultyofChemistry,InstituteofBiologicalChemistry,University
ofVienna,Vienna,Austria
JOHNOFFER • TheFrancisCrickInstitute,London,UK
GEORGEPAPAGEORGIOU • TheFrancisCrickInstitute,London,UK
ALLANM.PRIOR • DepartmentofPharmaceuticalSciences,TheDanielK.InouyeCollegeof
Pharmacy,UniversityofHawaiiatHilo,Hilo,HI,USA
RICHARDRAZ • TheFrancisCrickInstitute,London,UK
ANGELAA.SALIM • InstituteforMolecularBioscience,UniversityofQueensland,Brisbane,
QLD,Australia
JAKUB P.SE˛K • FacultyofChemistry,UniversityofWarsaw,Warsaw,Poland
SANDEEPK.SINGH • CEMCorporation,Matthews,NC,USA
MARIUSZSKWARCZYNSKI • SchoolofChemistryandMolecularBiosciences,TheUniversityof
Queensland,St.Lucia,QLD,Australia
RACHELJ.STEPHENSON • SchoolofChemistryandMolecularBiosciences,TheUniversityof
Queensland,St.Lucia,QLD,Australia
DIANQINGSUN • DepartmentofPharmaceuticalSciences,TheDanielK.InouyeCollegeof
Pharmacy,UniversityofHawaiiatHilo,Hilo,HI,USA
FENGTANG • CASKeyLaboratoryofReceptorResearch,CASCenter forExcellencein
MolecularCellScience,ShanghaiInstituteofMateriaMedica,ChineseAcademyof
Sciences,Shanghai,China;UniversityofChineseAcademyofSciences,Beijing,China