Total chemical synthesis of human thyroid-stimulating hormone (hTSH) β-subunit: Application of arginine-tagged acetamidomethyl (AcmR) protecting groups
John A. Brailsford, Jennifer L. Stockdill, Abram J. Axelrod, Michael T. Peterson, Paul A. Vadola, Eric V. Johnston, Samuel J. Danishefsky
Index: 10.1016/j.tet.2018.02.067
Full Text: HTML
Abstract
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.