Total chemical synthesis of human thyroid-stimulating hormone (hTSH) β-subunit: Application of arginine-tagged acetamidomethyl (AcmR) protecting groups

The β-subunit of human thyroid stimulating hormone (hTSH) has been synthesized as a single glycoform bearing a chitobiose disaccharide at the native glycosylation site. Key to the successful completion of this synthesis was the introduction of an arginine-tagged acetamidomethyl group, which served t...

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Published in:Tetrahedron 2018-04, Vol.74 (15), p.1951-1956
Main Authors: Brailsford, John A., Stockdill, Jennifer L., Axelrod, Abram J., Peterson, Michael T., Vadola, Paul A., Johnston, Eric V., Danishefsky, Samuel J.
Format: Article
Language:English
Subjects:
glycopeptides
Glycoprotein
glycosylation
humans
moieties
organic compounds
Peptide chemistry
solubility
synthesis
Thyroid-stimulating hormone
thyrotropin
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cited_by cdi_FETCH-LOGICAL-c484t-eede577a2b86f1102268a7741e16b604cc4ef9870d83097c19fc66e758f269d93
cites cdi_FETCH-LOGICAL-c484t-eede577a2b86f1102268a7741e16b604cc4ef9870d83097c19fc66e758f269d93
container_end_page 1956
container_issue 15
container_start_page 1951
container_title Tetrahedron
container_volume 74
creator Brailsford, John A.
Stockdill, Jennifer L.
Axelrod, Abram J.
Peterson, Michael T.
Vadola, Paul A.
Johnston, Eric V.
Danishefsky, Samuel J.
description The β-subunit of human thyroid stimulating hormone (hTSH) has been synthesized as a single glycoform bearing a chitobiose disaccharide at the native glycosylation site. Key to the successful completion of this synthesis was the introduction of an arginine-tagged acetamidomethyl group, which served to greatly facilitate handling of a glycopeptide fragment with poor aqueous solubility. This general solution to the challenge of working with intractable peptides is expected to find wide use in protein synthesis. [Display omitted]
doi_str_mv 10.1016/j.tet.2018.02.067
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source ScienceDirect Freedom Collection
subjects glycopeptides
Glycoprotein
glycosylation
humans
moieties
organic compounds
Peptide chemistry
solubility
synthesis
Thyroid-stimulating hormone
thyrotropin
title Total chemical synthesis of human thyroid-stimulating hormone (hTSH) β-subunit: Application of arginine-tagged acetamidomethyl (AcmR) protecting groups
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