Journal
CHEMICAL SCIENCE
Volume 2, Issue 9, Pages 1666-1676Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c1sc00185j
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Funding
- UCB Celltech
- European Commission
- Xunta de Galicia, Spain
- FCT, Portugal
- EPSRC
- BBSRC [BB/E004350/1] Funding Source: UKRI
- EPSRC [EP/I500200/1, EP/G026688/1, EP/E000614/1] Funding Source: UKRI
- Biotechnology and Biological Sciences Research Council [BB/C510824/1, EGA17763, BB/E004350/1] Funding Source: researchfish
- Engineering and Physical Sciences Research Council [EP/D023335/1, EP/G026688/1, GR/T26542/01, EP/E000614/1, EP/D023343/1, EP/I500200/1] Funding Source: researchfish
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Dehydroalanine is a synthetic precursor to a wide array of protein modifications. We describe multiple methods for the chemical conversion of cysteine to dehydroalanine on peptides and proteins. The scope and limitations of these methods were investigated with attention paid to side reactions, scale, and aqueous- and bio-compatibility. The most general method investigated-a bis-alkylation-elimination of cysteine to dehydroalanine-was applied successfully to multiple proteins and enabled the site-selective synthesis of a glycosylated antibody.
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