Journal
ORGANIC LETTERS
Volume 2, Issue 23, Pages 3603-3606Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol006485d
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- NCRR NIH HHS [1S10RR10444] Funding Source: Medline
- NIGMS NIH HHS [GM58822] Funding Source: Medline
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[GRAPHICS] Useful methodology is described for the synthesis of dehydroalanine residues (II) within peptides. The unnatural amino acid (Se)-phenylselenocysteine (I) can be incorporated into growing peptide chains via standard peptide synthesis procedures. Subsequent oxidative elimination affords a dehydroalanine at the desired position. The oxidation conditions are mild and tolerate functionalities commonly found in peptides, including variously protected cysteine residues. To illustrate its utility, cyclic lanthionines have been synthesized by this method.
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