Cyclotide Structures Revealed by NMR, with a Little Help from X‐ray Crystallography

ChemBioChem - Tập 21 Số 24 - Trang 3463-3475 - 2020
Thomas N. G. Handley1, Conan K. Wang1, Peta J. Harvey1, Nicole Lawrence1, David J. Craik1
1Institute for Molecular Bioscience, Australian Research Council Centre of Excellence for Innovations in Peptide and Protein Science, The University of Queensland, Brisbane, Queensland, 4072, Australia

Tóm tắt

Abstract

This review highlights the predominant role that NMR has had in determining the structures of cyclotides, a fascinating class of macrocyclic peptides found in plants. Cyclotides contain a cystine knot, a compact structural motif that is constrained by three disulfide bonds and able to resist chemical and biological degradation. Their resistance to proteolytic degradation has made cyclotides appealing as drug leads. Herein, we examine the developments that led to the identification and conclusive determination of the disulfide connectivity of cyclotides and describe in detail the structural features of exemplar cyclotides. We also review the role that X‐ray crystallography has played in resolving cyclotide structures and describe how racemic crystallography opened up the possibility of obtaining previously inaccessible X‐ray structures of cyclotides.

Từ khóa


Tài liệu tham khảo

10.1006/jmbi.1999.3383

10.1021/acs.chemrev.9b00402

 

10.1002/psc.1076

10.1002/anie.198205121

10.1016/j.bmc.2017.08.031

10.1002/anie.201807298

10.1021/acs.jmedchem.8b01588

 

10.1111/j.1600-0773.1973.tb01541.x

10.1021/ja00099a064

10.1021/np50114a002

 

10.1021/bi00013a002

10.1021/bi049711q

10.1074/jbc.M211147200

10.1021/bi9929756

10.1021/bi0106639

10.1002/cbic.200900342

10.1074/jbc.M101666200

10.1111/nph.13789

10.1073/pnas.96.16.8913

10.4161/cbt.1.4.9

 

10.1021/np970342r

10.1021/np9803878

10.1016/S0040-4039(97)01271-9

10.1042/BJ20051691

10.1111/j.1742-4658.2006.05282.x

10.1074/jbc.M900021200

10.1002/cbic.201100450

10.1074/jbc.M112.421198

10.1002/anie.201406563

10.1002/ange.201406563

10.1007/s10989-018-9701-1

10.1039/b607324g

10.1186/1472-6807-8-54

10.1016/j.str.2008.02.023

10.1074/jbc.M113.528240

10.1038/srep12974

10.1002/cbic.200700357

10.1016/j.bpj.2009.06.032

10.1016/j.biocel.2007.06.016

10.1016/j.jmb.2009.10.028

10.1021/ja405108p

 

10.1042/BJ20060627

10.1021/bi2004153

10.1021/acs.jpcb.8b10649

10.1006/abbi.2002.2769

10.1021/bi047837h

10.1016/j.bbapap.2006.07.009

10.1016/j.jinorgbio.2008.01.018

10.1073/pnas.1311183110

10.1073/pnas.1103660108

10.1021/acs.jnatprod.8b00572

10.1071/CH10007

10.1002/bip.21409

10.1042/BJ20051371

10.1006/jmbi.1998.2276

10.1007/s10989-004-1722-2

10.1128/JB.185.14.4011-4021.2003

10.1016/j.str.2003.11.019

10.1016/j.str.2005.02.013

10.1074/jbc.M501737200

10.1105/tpc.104.021790

10.1021/acschembio.8b00653

10.1074/jbc.M210492200

10.1021/bi027323n

10.1002/cbic.201402144

10.1074/jbc.M113.539262

10.1016/j.bbamem.2016.02.013

10.1074/jbc.M112.395442

10.1074/jbc.M308771200

10.1016/0079-6565(90)80003-Z

10.1021/ja8013538

10.1093/nar/gkh340

10.1007/s00018-005-5486-4

10.1016/j.bpj.2016.12.040

10.1002/cbic.200700187

10.1515/BC.2005.148