Greening Fmoc/tBu solid-phase peptide synthesis
File(s)10.1039@C9GC03982A.pdf (1.35 MB)
Accepted version
Author(s)
Al Musaimi, Othman
de la Torre, Beatriz G
Albericio, Fernando
Type
Journal Article
Abstract
Peptides are gaining considerable attention as potential drugs. The so-called Fmoc/tBu solid-phase synthesis is the method of choice for the synthesis of these molecules in both research and industrial settings. This synthetic strategy involves a solid polymeric protecting group and allows the use of an excess of reagents to achieve quantitative yields. Intermediates are not isolated. However, extensive washing with solvents is carried out between the synthetic steps. Hazardous solvents, mainly DMF, NMP, and CH2Cl2, are currently being used for the chemical reactions and also for the washings. In recent years, several studies have proposed the use of greener solvents in solid-phase peptide synthesis (SPPS). Here we compile all the greening efforts done in this regard and analyze each synthetic step separately. In summary, we can conclude that in many cases green solvents do not impair the synthetic process and that their adoption in current synthetic schemes will be translated into a smaller impact on the environment and on human health.
Date Issued
2020-02-21
Date Acceptance
2020-01-24
Citation
Green Chemistry, 2020, 22 (4), pp.996-1018
ISSN
1463-9262
Publisher
Royal Society of Chemistry
Start Page
996
End Page
1018
Journal / Book Title
Green Chemistry
Volume
22
Issue
4
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:000518034000001&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=1ba7043ffcc86c417c072aa74d649202
Subjects
Science & Technology
Physical Sciences
Chemistry, Multidisciplinary
Green & Sustainable Science & Technology
Chemistry
Science & Technology - Other Topics
CYCLOPENTYL METHYL-ETHER
N-PROTECTING GROUP
CHEMISTRY RESEARCH AREAS
GAMMA-VALEROLACTONE GVL
WATER-BASED SYNTHESIS
AMINO-ACIDS
COUPLING REAGENTS
SOLVENT
TETRAFLUOROBORATE
PRECIPITATION
Publication Status
Published
Date Publish Online
2020-01-25