Paper - WANFANG MED ONLINE

You Position: Home > Paper

Recent progress in the improvement of the coupling efficiency of "difficult sequences" in peptide synthesis

( views:308, downloads:8 )

Author:: No author available

Journal Title:: ACTA PHARMACEUTICA SINICA

Issue:: 2

DOI:: 10.3321/j.issn:0513-4870.2007.02.001

Key Word:: 多肽合成;缩合效率;困难序列;β-构象;peptide synthesis;coupling efficiency;difficult sequences;β-structure of peptide

Abstract： Even though chemistry is now in place that potentially allows high coupling efficiencies to be attained, successful coupling is usually a challenge when so-called "difficult sequences" is encountered in peptide synthesis. Some factors that affect the coupling efficiency have been discussed and related methods to overcome those obstacles have been introduced in present review. All suggestions proposed here are valuable and also feasible to improve the coupling completeness in both liquid-phase or solid-phase peptide synthesis.

Reference

[1]HISAYA KURODA,YUN-NENG CHEN,TERUTOSHI KIMURA,etc.Powerful solvent systems useful for synthesis of sparingly-soluble peptides in solution[J].1992,40(3‐4).
[2]Holm A,Due-Larsen B.Sequence-assisted peptide synthesis (SAPS).[J].1998,52(6).
[3]Miranda LP.,Smythe ML.,Alewood PF.,etc.Activated O -> N acyl transfer auxiliary: Efficient amide-backbone substitution of hindered "difficult" peptides[J].2000,65(18).
[4]Z, Wu,B, Ericksen,K, Tucker,etc.Synthesis and characterization of human alpha-defensins 4-6.[J].2004,64.
[5]Carpino, L. A.,Krause, E.,Sferdean, C. D.,etc.Synthesis of??????difficult?????? peptide sequences: application of a depsipeptide technique to the Jung??????Redemann 10- and 26-mers and the amyloid peptide A????(1??????42)[J].2004,45(40).
[6]Alma DalPozzo,Minghong Ni,Laura Muzi,etc.Amino Acid Bromides: Their N-Protection and Use in the Synthesis of Peptides with Extremely Difficult Sequences[J].2002,67(18).
[7]Alewood PF.,Miranda LP..Challenges for protein chemical synthesis in the 21st century: Bridging genomics and proteomics[J].2000,55(3).
[8]Mammi S,Peggion E,van-Gunsteren W,etc.Conformational study of an Aib-rich peptide in DMSO by NMR.[J].2001,57(2).
[9]Wade JD,Macris M,Clippingdale AB,etc.Synthesis and secondary structural studies of penta(acetyl-Hmb)A beta(1-40).[J].1999,53(6).
[10]L M, Varanda,M T, Miranda.Solid-phase peptide synthesis at elevated temperatures: a search for and optimized synthesis condition of unsulfated cholecystokinin-12.[J].1997,50.
[11]王德心主编.SOLIDPHASE ORGANIC SYNTHESIS[M].2004.
[12]C K, Taylor,P W, Abel,M, Hulce,etc.Solvent effects on coupling yields during rapid solid-phase synthesis of CGRP(8-37) employing in situ neutralization.[J].2005,65(1).
[13]Bacsa B,Desai B,Dibo G,etc.Rapid solid-phase peptide synthesis using thermal and controlled microwave irradiation[J].2006,12(10).
[14]Anna K, Tickler,Andrew B, Clippingdale,John D, Wade.Amyloid-beta as a "difficult sequence" in solid phase peptide synthesis.[J].2004,11.
[15]Palasek SA,Cox ZJ,Collins JM.Limiting racemization and aspartimide formation in microwave-enhanced Fmoc solid phase peptide synthesis[J].2007,13(3).
[16]Kevin Bailey,Graham Bloomberg,Peter White,etc.Expediting the Fmoc solid phase synthesis of long peptides through the application of dimethyloxazolidine dipeptides[J].2004,10(1).
[17]Eduardo M. Cilli,Eliandre Oliveira,Reinaldo Marchetto,etc.Correlation between Solvation of Peptide-Resins and Solvent Properties[J].1996,61(25).
[18]King-D S,Prusiner-S B,Cohen-F E,etc.Engineering the prion protein using chemical synthesis.[J].2001,58(5).
[19]Bradley Mark,May Peter J.,Harrowven David C..A new method of forming resin bound thioesters and their use as 'traceless'linkers in solid phase synthesis[J].2000,41(10).
[20]Tzavara C,Gatos D.Comparison of the solid-phase fragment condensation and phase-change approaches in the synthesis of salmon I calcitonin.[J].2001,57(2).
[21]M, Mutter,A, Nefzi,T, Sato,etc.Pseudo-prolines (psi Pro) for accessing "inaccessible" peptides.[J].1900,8.
[22]Sohma, Y.,Sasaki, M.,Hayashi, Y.,etc.Design and synthesis of a novel water-soluble Ab1-42 isopeptide: an efficient strategy for the preparation of Alzheimer's disease-related peptide, Ab1-42, via O-N intramolecular acyl migration reaction[J].2004,45(31).
[23]Wim D. F. Meutermans,Simon W. Golding,David Craik,etc.Difficult Macrocyclizations: New Strategies for Synthesizing Highly Strained Cyclic Tetrapeptides[J].2003,5(15).
[24]H, Brückner,A, Koza.Solution phase synthesis of the 14-residue peptaibol antibiotic trichovirin I.[J].2003,24(3).
[25]B, Yan.The properties of resin supports and their effects on solid-phase organic synthesis.[J].1998,1.
[26]A K, Tickler,C J, Barrow,J D, Wade.Improved preparation of amyloid-beta peptides using DBU as Nalpha-Fmoc deprotection reagent.[J].2001,7.
[27]M, Teixidó,F, Albericio,E, Giralt.Solid-phase synthesis and characterization of N-methyl-rich peptides.[J].2005,65(2).
[28]Albericio F,Garcia-Martin F,Quintanar-Audelo M,etc.ChemMatrix, a poly(ethylene glycol)-based support for the solid-phase synthesis of complex peptides[J].2006,8(2).
[29]Nishiuchi Y,Kimura T,Inui T,etc.Solution synthesis and biological activity of human pleiotrophin, a novel heparin-binding neurotrophic factor consisting of 136 amino acid residues with five disulfide bonds.[J].2000,55(5).
[30]Cilli EM,Crusca E,Almeida FCL,etc.Study of the effect of the peptide loading and solvent system in SPPS by HRMAS-NMR[J].2005,11(9).
[31]W R, Sampson,H, Patsiouras,N J, Ede.The synthesis of 'difficult' peptides using 2-hydroxy-4-methoxybenzyl or pseudoproline amino acid building blocks: a comparative study.[J].1999,5.
[32]M W, Pennington,I, Zadenberg,M E, Byrnes,etc.Synthesis of the cardiac inotropic polypeptide anthopleurin-A.[J].1994,43(5).