Amino Acids, Peptides and Proteins (SPR Amino Acids, Peptides, and Proteins (RSC)) (Vol 36) PDF
Preview Amino Acids, Peptides and Proteins (SPR Amino Acids, Peptides, and Proteins (RSC)) (Vol 36)
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 Ifyoubuythistitleonstandingorder,youwillbegivenFREEaccess to the chapters online. Please contact [email protected] with proof of purchase to arrange access to be set up. Thank you 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 All rights reserved Apart from any fair dealing for the purpose of research or private study, or criticismorreviewaspermittedunderthetermsoftheUKCopyright,Designs and Patents Act, 1988, this publication may not be reproduced, stored or transmitted, in any form or by any means, without the prior permission in writing of The Royal Society of Chemistry, or in the case of reprographic reproduction only in accordance with the terms of the licences issued by the CopyrightLicensingAgencyintheUK,orinaccordancewiththetermsofthe licences issued by the appropriate Reproduction Rights Organization outside theUK.Enquiriesconcerningreproductionoutsidethetermsstatedhereshould besenttoTheRoyalSocietyofChemistryattheaddressprintedonthispage. Published by The Royal Society of Chemistry, Thomas Graham House, Science Park, Milton Road, Cambridge CB4 0WF, UK Registered Charity Number 207890 For further information see our web site at www.rsc.org Typeset by Macmillan India Ltd, Bangalore, India Printed by Henry LingLtd, Dorchester,Dorset,UK 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 Thisjournalis(cid:1)c TheRoyalSocietyofChemistry2007 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 Thisjournalis(cid:1)c TheRoyalSocietyofChemistry2007 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 Thisjournalis(cid:1)c TheRoyalSocietyofChemistry2007 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 Thisjournalis(cid:1)c TheRoyalSocietyofChemistry2007
Description:The list of books you might like
