2-Methyltetrahydrofuran and cyclopentyl methyl ether for green solid-phase peptide synthesis

被引：0
作者：
Yahya E. Jad
Gerardo A. Acosta
Sherine N. Khattab
Beatriz G. de la Torre
Thavendran Govender
Hendrik G. Kruger
Ayman El-Faham
Fernando Albericio
机构：
[1] University of KwaZulu-Natal,Catalysis and Peptide Research Unit, School of Health Sciences
[2] Institute for Research in Biomedicine-Barcelona,CIBER
[3] Networking Centre on Bioengineering,BBN
[4] Biomaterials and Nanomedicine,Department of Chemistry, Faculty of Science
[5] Alexandria University,Department of Chemistry, College of Science
[6] King Saud University,School of Chemistry and Physics
[7] University of KwaZulu-Natal,Department of Organic Chemistry
[8] University of Barcelona,undefined
来源：
Amino Acids | 2016年 / 48卷
关键词：
Green solvents; Solid-phase peptide synthesis; Peptide synthesis; 2-methyltetrahydrofuran; Cyclopentyl methyl ether;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
2-MeTHF and CPME were evaluated as greener alternatives for the most employed solvents in peptide synthesis. The ability of these solvents to dissolve amino acid derivatives and a range of coupling reagents were evaluated as well as the swelling of polystyrene and polyethylene glycol resins. In addition, racemization and coupling efficiencies were also determined. We concluded that the use of 2-MeTHF with combination of DIC/OxymaPure gave the lowest racemization level during stepwise synthesis of Z-Phg-Pro-NH2 and the highest purity during SPPS of Aib-enkephalin pentapeptide (H-Tyr-Aib-Aib-Phe-Leu-NH2).
引用
收藏
页码：419 / 426
页数：7
相关论文
共 108 条
[1]  
Acosta GA(2009)Solid-phase peptide synthesis using acetonitrile as a solvent in combination with PEG-based resins J Pept Sci 15 629-633
[2]  
del Fresno M(2013)Development of GSK’s reagent guides—embedding sustainability into reagent selection Green Chem 15 1542-1549
[3]  
Paradis-Bas M(2004)Developments in peptide and amide synthesis Curr Opin Chem Biol 8 211-221
[4]  
Rigau-DeLlobet M(2012)Therapeutic peptides Future Med Chem 4 1527-1531
[5]  
Cote S(2008)Green chemistry tools to influence a medicinal chemistry and research chemistry based organisation Green Chem 10 31-36
[6]  
Royo M(2011)Toxicological assessment of 2-methyltetrahydrofuran and cyclopentyl methyl ether in support of their use in pharmaceutical chemical process development Org Process Res Dev 15 939-941
[7]  
Albericio F(2010)Critical evaluation of in situ coupling reagents for SPPS J Pept Sci 16 71-43
[8]  
Adams JP(2004)From production of peptides in milligram amounts for research to multi-tons quantities for drugs of the future Curr Pharm Biotechnol 5 29-4398
[9]  
Albericio F(1993)1-Hydroxy-7-azabenzotriazole. An efficient peptide coupling additive J Am Chem Soc 115 4397-137
[10]  
Albericio F(1994)Advantageous applications of azabenzotriazole (triazolopyridine)-based coupling reagents to solid-phase peptide synthesis J Chem Soc Chem Commun 11 133-1272
12345678910