Literature DB >> 26403847

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

Yahya E Jad1, Gerardo A Acosta2,3, Sherine N Khattab4, Beatriz G de la Torre1, Thavendran Govender1, Hendrik G Kruger1, Ayman El-Faham5,6, Fernando Albericio7,8,9,10,11,12.   

Abstract

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).

Entities:  

Keywords:  2-methyltetrahydrofuran; Cyclopentyl methyl ether; Green solvents; Peptide synthesis; Solid-phase peptide synthesis

Mesh:

Substances:

Year:  2015        PMID: 26403847     DOI: 10.1007/s00726-015-2095-x

Source DB:  PubMed          Journal:  Amino Acids        ISSN: 0939-4451            Impact factor:   3.520


  6 in total

Review 1.  Greening the synthesis of peptide therapeutics: an industrial perspective.

Authors:  Vincent Martin; Peter H G Egelund; Henrik Johansson; Sebastian Thordal Le Quement; Felix Wojcik; Daniel Sejer Pedersen
Journal:  RSC Adv       Date:  2020-11-24       Impact factor: 4.036

2.  Sustainable Peptide Synthesis Enabled by a Transient Protecting Group.

Authors:  Sascha Knauer; Niklas Koch; Christina Uth; Reinhard Meusinger; Olga Avrutina; Harald Kolmar
Journal:  Angew Chem Int Ed Engl       Date:  2020-05-29       Impact factor: 15.336

3.  Scope and Limitations of γ-Valerolactone (GVL) as a Green Solvent to be Used with Base for Fmoc Removal in Solid Phase Peptide Synthesis.

Authors:  Ashish Kumar; Anamika Sharma; Beatriz G de la Torre; Fernando Albericio
Journal:  Molecules       Date:  2019-11-05       Impact factor: 4.411

Review 4.  Amide Bonds Meet Flow Chemistry: A Journey into Methodologies and Sustainable Evolution.

Authors:  Antonella Ilenia Alfano; Heiko Lange; Margherita Brindisi
Journal:  ChemSusChem       Date:  2022-02-01       Impact factor: 9.140

Review 5.  Cyclopentyl Methyl Ether: An Elective Ecofriendly Ethereal Solvent in Classical and Modern Organic Chemistry.

Authors:  Ugo Azzena; Massimo Carraro; Luisa Pisano; Serena Monticelli; Roberta Bartolotta; Vittorio Pace
Journal:  ChemSusChem       Date:  2018-11-20       Impact factor: 8.928

6.  A Simple, Efficient, and Eco-Friendly Method for the Preparation of 3-Substituted-2,3-dihydroquinazolin-4(1H)-one Derivatives.

Authors:  Zainab Almarhoon; Kholood A Dahlous; Rakia Abd Alhameed; Hazem A Ghabbour; Ayman El-Faham
Journal:  Molecules       Date:  2019-11-09       Impact factor: 4.411

  6 in total

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