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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Bibliographic Details
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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Summary: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]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.02.067