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Ethyl substituted coumarin-4-yl derivatives as photoremovable protecting groups for amino acids with improved stability for SPPS

Paper ID Volume ID Publish Year Pages File Format Full-Text
26958 43989 2012 6 PDF Available
Title
Ethyl substituted coumarin-4-yl derivatives as photoremovable protecting groups for amino acids with improved stability for SPPS
Abstract

The synthesis, photochemical properties and chemical stability of 7-(N,N-diethylamino-coumarin-4-yl)-1-ethyl (DEACE) photoremovable protecting group for carboxylic acids are presented. We demonstrate that the ethyl substituent of DEACE improves the hydrolytic stability of the protected ester in basic conditions used in solid phase peptide synthesis (SPPS) and retains the good photochemical properties of the coumarin-4-yl methyl derivatives. DEACE allows the preparation of peptides with protected carboxylic side groups with high yield via SPPS.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► A methylated derivative of a coumarin-4-yl photosensitive cage was synthesized. ► Methyl substitution retains the photochemical properties of the coumarin-4-yl cage. ► Aspartic acid was modified with the new cage at the side chain carboxylic acid group. ► Methyl substitution enhances the stability of the ester bond during SPPS.

Keywords
Photoremovable protecting group; Coumarin; Phototriggers; Caged peptides
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Ethyl substituted coumarin-4-yl derivatives as photoremovable protecting groups for amino acids with improved stability for SPPS
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 241, 1 August 2012, Pages 52–57
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us