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Multiple-turnover isotopic labeling of Fmoc- and Boc-protected amino acids with oxygen isotopes


Seyfried, M S; Lauber, B S; Luedtke, N W (2010). Multiple-turnover isotopic labeling of Fmoc- and Boc-protected amino acids with oxygen isotopes. Organic Letters, 12(1):104-106.

Abstract

An efficient method for the selective isotopic labeling of carboxylic acids is reported. By reacting an amino acid with excess carbodiimide and 18O-H2O, a kinetically enhanced multiple turnover reaction provides the 18O-labeled product in high yield and excellent isotopic enrichment. This reaction is fully compatible with standard Fmoc, Boc, Trt, and OtBu protecting groups and provides a means to selectively label the α-carboxylic acids of functionalized amino acids with stable oxygen isotopes.

Abstract

An efficient method for the selective isotopic labeling of carboxylic acids is reported. By reacting an amino acid with excess carbodiimide and 18O-H2O, a kinetically enhanced multiple turnover reaction provides the 18O-labeled product in high yield and excellent isotopic enrichment. This reaction is fully compatible with standard Fmoc, Boc, Trt, and OtBu protecting groups and provides a means to selectively label the α-carboxylic acids of functionalized amino acids with stable oxygen isotopes.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2010
Deposited On:24 Jan 2010 11:17
Last Modified:17 Feb 2018 16:50
Publisher:American Chemical Society
ISSN:1523-7052
Additional Information:Publication Date (Web): November 30, 2009
OA Status:Closed
Publisher DOI:https://doi.org/10.1021/ol902519g
PubMed ID:20035564

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