Tetrahedron 2018-03-06

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.

Latest Articles:

Synthesis of chiral α-amino anilides via a DMEDA-promoted selective C─N coupling reaction of aryl halides and α-aminoamides

2018-04-11

[10.1016/j.tet.2018.03.003]

A site isolation-enabled organocatalytic approach to enantiopure γ-amino alcohol drugs

2018-04-11

[10.1016/j.tet.2018.04.022]

Chemoselectivity in the Kosugi-Migita-Stille coupling of bromophenyl triflates and bromo-nitrophenyl triflates with (ethenyl)tributyltin

2018-04-10

[10.1016/j.tet.2018.02.051]

Process design methodology for organometallic chemistry in continuous flow systems

2018-04-07

[10.1016/j.tet.2018.04.020]

Substrate engineering: Effects of different N-protecting groups in the CAL-B-catalysed asymmetric O-acylation of 1-hydroxymethyl-tetrahydro-β-carbolines

2018-04-07

[10.1016/j.tet.2018.04.012]

More Articles...