Total chemical synthesis of human thyroid-stimulating hormone (hTSH) β-subunit: Application of arginine-tagged acetamidomethyl (Acm(R)) protecting groups Journal Article
| Authors: | Brailsford, J. A.; Stockdill, J. L.; Axelrod, A. J.; Peterson, M. T.; Vadola, P. A.; Johnston, E. V.; Danishefsky, S. J. |
| Article Title: | Total chemical synthesis of human thyroid-stimulating hormone (hTSH) β-subunit: Application of arginine-tagged acetamidomethyl (Acm(R)) protecting groups |
| 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. © 2018 Elsevier Ltd |
| Keywords: | glycoprotein; thyroid-stimulating hormone; peptide chemistry |
| Journal Title: | Tetrahedron |
| Volume: | 74 |
| Issue: | 15 |
| ISSN: | 0040-4020 |
| Publisher: | Elsevier Inc. |
| Date Published: | 2018-04-12 |
| Start Page: | 1951 |
| End Page: | 1956 |
| Language: | English |
| DOI: | 10.1016/j.tet.2018.02.067 |
| PROVIDER: | scopus |
| PMCID: | PMC6402344 |
| PUBMED: | 30853725 |
| DOI/URL: | |
| Notes: | Article -- Export Date: 2 April 2018 -- Source: Scopus |
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539Danishefsky -
5Vadola -
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Johnston -
3
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4Axelrod
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