Amino Acids, Peptides and Proteins (SPR Amino Acids, Peptides, and Proteins (RSC)) (Vol 36)

345 Pages·2007·5.66 MB·English

by  John S. Davies

Amino Acids, Peptides and Proteins
Volume 36

A Specialist Periodical Report
Amino Acids, Peptides and Proteins
Volume 36
A Review of the Literature Published during 2003–2004.
Editor
J.S. Davies, University of Wales, Swansea, UK
Authors
D.T. Elmore, Oxfordshire, UK
E. Farkas, University of Debrecen, Hungary
B. Penke, University Szeged, Hungary
I. So´va´go´, University of Debrecen, Hungary
G. To´th, University Szeged, Hungary
G. Va´radi, University Szeged, Hungary
M. Zarandi, University Szeged, Hungary
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ISBN 978-0-85404-252-4
ISSN 1361-5904
A catalogue record for this book is available from the British Library
r The Royal Society of Chemistry 2007
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Preface
DOI: 10.1039/b710329h
DrGeoffreyYoung,aseditorofthefirstvolumeinthisseriesin1968,commented
that‘onecouldhardlyaskforamoreexcitingtimeatwhichtoreviewthefield’.Asa
Chapterauthor,sincethoseearlydays,Ihaveseentheexcitingtimescontinueand
themanyvolumesinthisserieshavebeenpartytogreatdevelopmentsinthefield.
Solid phase synthesis, in its infancy in 1968, has revolutionised the making and
manufacturingofpeptidesandnodoubtthenumberandcomplexityofthepeptides
beingmadethesedayscanonlyhavebeendreamtof40yearsago.Theavailabilityof
clonedproteinshasmadeavailablemolecularreceptors, thatnowcanroutinely be
usedinmolecularrecognitionstudies,sothatthedevelopmentofefficientinhibitors
hasamuchmorerationalbasis.Theprinciplesofsolidphasepeptidesynthesishave
spawnednotonlyanewapproachtoenhancingthepoolofpeptidesavailable,but
also the discipline of combinatorial chemistry. Numerous novel amino acids have
beenidentified,andresearchinmolecularrecognitionhasincreasedthedemandfor
novel non-proteinogenic amino acids. Thus developments in asymmetric synthesis
havefoundexcellentopportunitiesintheaminoacidcontext,whosesynthesesnow
dependlessonthetraditionalresolutionofsynthesisedracemates.
These Specialist Reports have co-existed with the establishment of major inter-
nationalpeptidesocieties,theAmerican,EuropeanandJapanesePeptideSocieties,
and their associated Journals. These have been instrumental in promoting the
developments in amino acids, peptides and proteins across a very broad spectrum
ofactivitythattranscendsthefrontiersbetweenchemistryandbiology.
Thisvastexpansionofthefieldhasinevitablyplacedagreatdealmorepressureon
the reporting authors. Yes, computational scanning of the literature has aided the
harvestingofpapers,buthasdonelittletoassisttheimportantphaseofplacingin
contextthe truesignificanceofthedevelopments inthefield.Thisisaburdenthat
has little recognition, so as I pass on the mantle of Senior Reporter to others, I
empathisewithandsalutethehardworkofcolleagueswhohavegivenlonghoursof
endeavourtoproducechaptersthatareavailableforyoutoreadwithinthecoversof
theseSPRs.
ThisparticularVolume hasaimedtobringthereviewcoverageuptotheendof
2004, and therefore concentrates on the publications of 2003–4. This has brought
more pressures of space on the authors, which has meant more selectivity in the
selection of papers for review. The recent years have coincided with the ebbing of
peptideresearchintheUK,withfewerresearchgroupsfromwhichreviewauthors
could be drawn. This Volume has been made possible by the significant input of
Hungariancolleagues,BotondPenke,Ga´borTo´thGyo¨rgyiVa´radi,MartaZarandi,
Etelka Farkas and Imre So´va´go´ augmenting the continuing efforts of Donald
ElmoreandJohnDavies overmanyyears.WeallhopethatthisSPRoffersatrue
reflectionof the vastareaofactivityworldwide.Wewouldhavepreferreda better
timeframetopublication,butcriticaldelayshavebeenbroughtaboutbypressureof
work.
Wehaveaimedtopromotegoodstandardsofnomenclature,sowehavebeenvery
grateful for Dr John Jones’s unceasing effort to preserve standards and invite the
bestfromothers.Wearegratefulforhiswillingnesstoallowhiscontributionstobe
compiledwithinthemanyVolumesofthisseries.Wealsoappreciatetheassistance
of RSC Publishing staff, and we can only hope that the series in its own way
contributes to the exciting developments in this field, and prevented many a
‘rediscovery of the wheel’, which can happen, if the literature is not adequately
andthoroughlysurveyed.
JohnS.Davies
Swansea,2007
AminoAcids,Pept.Proteins,2007,36,7 | 7
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CONTENTS
Cover
Thecrystalstructureof
particulatemethane
monooxygenase(pMMO)
revealsmanyunexpected
featuresincluding,atrimeric
oligomerizationstateandthree
distinctmetalcenters.
Imagereproducedbypermis-
sionofAmyRosenzweigfrom
DaltonTransactions,2005.
Preface 7
John S. Davies
Amino acids 19
Marta Zarandi
Introduction 19
Naturally occuring amino acids 19
Chemical synthesis and resolution of amino acids 22
Physical and stereochemical studies of amino acids 59
Chemical studies of amino acids 60
Analytical methods 63
Peptide synthesis 82
Donald T. Elmore
Introduction 82
Methods 82
Appendix: A list of syntheses in 2003–2004 98
AminoAcids,Pept.Proteins,2007,36,9–10 | 9
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Analogue and conformational studies on peptides, hormones and other 131
biologically active peptides
Botond Penke, Ga´bor To´th and Gyo¨rgyi Va´radi
Introduction 131
Peptide backbone modifications and peptide mimetics 131
Cyclic peptides 139
Biologically active peptides 141
Enzyme inhibitors 176
Phage library leads 206
Protein–protein interaction inhibitors: SH2 and SH3 domain 206
ligands
Cyclic, modified and conjugated peptides 227
John S. Davies
Introduction 227
Cyclic peptides 227
Modified and conjugated peptides 257
Miscellaneous structures 271
Metal complexes of amino acids and peptides 287
E. Farkas and I. So´va´go´
Introduction 287
Amino acid complexes 288
Peptide complexes 312
10 | AminoAcids,Pept.Proteins,2007,36,9–10
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A Short Guide to Abbreviations and Their Use in
Peptide Science
Abbreviations,acronymsandsymbolicrepresentationsareverymuchpartof
the language ofpeptide science – inconversational communication asmuch
asinitsliterature.They are not onlyaconvenience,either– theyenablethe
necessary but distracting complexities of long chemical names and technical
termstobepushedintothebackgroundsothewoodcanbeseenamongthe
trees. Many of the abbreviations in use are so much in currency that they
need no explanation. The main purpose of this editorial is to identify them
and free authors from the hitherto tiresome requirement to define them in
everypaper.Thoseinthetablesthatfollow–whichwillbeupdatedfromtime
to time – may in future be used in thisJournalwithout explanation.
All other abbreviations should be defined. Previously published usage
shouldbefollowedunlessitismanifestlyclumsyorinappropriate.Whereit
isnecessarytodevisenewabbreviationsandsymbols,thegeneralprinciples
behind established examples should be followed. Thus, new amino-acid
symbols should be of form Abc, with due thought for possible ambiguities
(Dap might be obvious for diaminoproprionic acid, for example, but what
about diaminopimelic acid?).
Where alternatives are indicated below, the first is preferred.
Amino Acids
Proteinogenic Amino Acids
Ala Alanine A
Arg Arginine R
Asn Asparagine N
Asp Aspartic acid D
Asx Asn or Asp
Cys Cysteine C
Gln Glutamine Q
Glu Glutamic acid E
Glx Gln or Glu
Gly Glycine G
His Histidine H
Ile Isoleucine I
Leu Leucine L
Lys Lysine K
Met Methionine M
Phe Phenylalanine F
Copyrightr1999EuropeanPeptideSocietyandJohnWiley&Sons,Ltd.Reproducedwith
permissionfromJ.PeptideSci.,1999,5,465–471.
AminoAcids,Pept.Proteins,2007,36,11–18 | 11
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