Cleaving protected peptides from 2-chlorotrityl chloride resin. Moving away from dichloromethane
File(s)
Published version
Author(s)
Alhassan, Mahama
Al Musaimi, Othman
Collins, Jonathan M
Albericio, Fernando
de la Torre, Beatriz G
Type
Journal Article
Abstract
In recent years, the work of various research groups has allowed the substitution of the hazardous solvents most widely used in solid-phase peptide synthesis, namely DMF, NMP, DCM, DEE, among others, by several much less hazardous solvents. Indeed, greener alternatives have been found for almost all steps of the process, with the exception of the cleavage of protected peptides from 2-chlorotrityl chloride resin. Here, after careful screening of several of the so-called green solvents, we propose 2% TFA in either anisole or 1,3-dimethoxybenzene as optimal for the cleavage step. The higher boiling point of these solvents compared with the DCM allows the preparation of protected peptides with less risk of premature removal of the most labile protecting groups, such as the Trt of His. Our findings once again evidence the value/versatility of green solvents in strict chemical terms.
Date Issued
2020-04-13
Date Acceptance
2020-04-10
Citation
Green Chemistry, 2020, 22 (9), pp.2840-2845
ISSN
1463-9262
Publisher
Royal Society of Chemistry
Start Page
2840
End Page
2845
Journal / Book Title
Green Chemistry
Volume
22
Issue
9
Copyright Statement
© The Royal Society of Chemistry 2020
Identifier
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000533979200016&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=1ba7043ffcc86c417c072aa74d649202
Subjects
Science & Technology
Physical Sciences
Chemistry, Multidisciplinary
Green & Sustainable Science & Technology
Chemistry
Science & Technology - Other Topics
GAMMA-VALEROLACTONE
GREEN SOLVENTS
PRECIPITATION
SELECTION
ACID
Publication Status
Published
Date Publish Online
2020-04-13