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Toward Homogeneous Erythropoietin: Application of Metal‐Free Dethiylation in the Chemical Synthesis of the Ala79‐Arg166 Glycopeptide Domain
Author(s) -
Dong Suwei,
Shang Shiying,
Tan Zhongping,
Danishefsky Samuel J.
Publication year - 2011
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.201100077
Subject(s) - chemistry , glycopeptide , native chemical ligation , cysteine , ligation , combinatorial chemistry , alanine , proline , amino acid , homogeneous , biochemistry , erythropoietin , chemical synthesis , recombinant dna , stereochemistry , in vitro , enzyme , microbiology and biotechnology , medicine , physics , thermodynamics , biology , antibiotics , gene
We describe herein the assembly of hEPO(79–166), a key glycopeptide segment en route to erythropoietin, in minimally protected form. Key to the success of this synthetic endeavor was the application of our two‐step cysteine‐free native chemical ligation strategy, by which we achieved formal ligation at alanine and proline residues through the use of an N‐terminal amino acid surrogate presenting a readily removable thiol functionality.