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Caged O-phosphorothioyl amino acids as building blocks for Fmoc-based solid phase peptide synthesis.

ABSTRACT: The synthesis of 1-(2-nitrophenylethyl) caged O-phosphorothioylserine, -threonine and -tyrosine derivatives is reported. These amino acid building blocks can be directly incorporated into peptides by Fmoc-based solid phase synthesis as their pentafluorophenyl esters or as symmetric anhydrides. Upon irradiation with UV light, the thiophosphate group, representing a hydrolysis resistant phosphate analog, is revealed.

SUBMITTER: Aemissegger A

PROVIDER: S-EPMC2699315 | biostudies-literature | 2007 Jul

REPOSITORIES: biostudies-literature

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Caged O-phosphorothioyl amino acids as building blocks for Fmoc-based solid phase peptide synthesis.

Aemissegger Andreas A Carrigan Christina N CN Imperiali Barbara B

Tetrahedron 20070701 27

The synthesis of 1-(2-nitrophenylethyl) caged O-phosphorothioylserine, -threonine and -tyrosine derivatives is reported. These amino acid building blocks can be directly incorporated into peptides by Fmoc-based solid phase synthesis as their pentafluorophenyl esters or as symmetric anhydrides. Upon irradiation with UV light, the thiophosphate group, representing a hydrolysis resistant phosphate analog, is revealed. ...[more]

PMID: 19543448

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