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Total Chemical Synthesis of Human Thyroid-Stimulating Hormone (hTSH) ?-Subunit: Application of Arginine-tagged Acetamidomethyl (AcmR) Protecting Groups.


ABSTRACT: The ?-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.

SUBMITTER: Brailsford JA 

PROVIDER: S-EPMC6402344 | biostudies-literature | 2018 Apr

REPOSITORIES: biostudies-literature

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Total Chemical Synthesis of Human Thyroid-Stimulating Hormone (hTSH) <i>β</i>-Subunit: Application of Arginine-tagged Acetamidomethyl (Acm<sup>R</sup>) Protecting Groups.

Brailsford John A JA   Stockdill Jennifer L JL   Axelrod Abram J AJ   Peterson Michael T MT   Vadola Paul A PA   Johnston Eric V EV   Danishefsky Samuel J SJ  

Tetrahedron 20180306 15


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 prote  ...[more]

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