Synthesis of a Selenocysteine-Containing Peptide by Native Chemical Ligation

A new method for the synthesis of selenocysteine derivatives and selenocysteine-containing peptides is described. Fmoc-Se-p-methoxybenzylselenocysteine (1) was prepared and used for solid-phase synthesis of peptides with an N-terminal unprotected selenocysteine. Subsequent native chemical ligation w...

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Bibliographic Details
Published in:Organic letters 2001-05, Vol.3 (9), p.1331-1334
Main Authors: Gieselman, Matt D, Xie, Lili, van der Donk, Wilfred A
Format: Article
Language:English
Subjects:
Magnetic Resonance Spectroscopy
Molecular Structure
Peptides - chemical synthesis
Peptides - chemistry
Ribonucleotide Reductases - chemistry
Selenocysteine - chemical synthesis
Selenocysteine - chemistry
Sequence Analysis, Protein
Sequence Homology, Amino Acid
Structure-Activity Relationship
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Summary:A new method for the synthesis of selenocysteine derivatives and selenocysteine-containing peptides is described. Fmoc-Se-p-methoxybenzylselenocysteine (1) was prepared and used for solid-phase synthesis of peptides with an N-terminal unprotected selenocysteine. Subsequent native chemical ligation with a peptide thioester provided a 17-mer that corresponds to the C-terminus of ribonucleotide reductase with selenocysteine in place of cysteine.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol015712o