Literature DB >> 30853725

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

John A Brailsford1, Jennifer L Stockdill1, Abram J Axelrod1, Michael T Peterson1, Paul A Vadola1, Eric V Johnston1, Samuel J Danishefsky1.   

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.

Entities:  

Year:  2018        PMID: 30853725      PMCID: PMC6402344          DOI: 10.1016/j.tet.2018.02.067

Source DB:  PubMed          Journal:  Tetrahedron        ISSN: 0040-4020            Impact factor:   2.457


  31 in total

1.  Covalent capture: a new tool for the purification of synthetic and recombinant polypeptides.

Authors:  M Villain; J Vizzavona; K Rose
Journal:  Chem Biol       Date:  2001-07

2.  Synthesis of the C-terminal region of opioid receptor like 1 in an SDS micelle by the native chemical ligation: effect of thiol additive and SDS concentration on ligation efficiency.

Authors:  Takeshi Sato; Yasuhiro Saito; Saburo Aimoto
Journal:  J Pept Sci       Date:  2005-07       Impact factor: 1.905

3.  Kinetically controlled ligation for the convergent chemical synthesis of proteins.

Authors:  Duhee Bang; Brad L Pentelute; Stephen B H Kent
Journal:  Angew Chem Int Ed Engl       Date:  2006-06-12       Impact factor: 15.336

Review 4.  Amino acid-protecting groups.

Authors:  Albert Isidro-Llobet; Mercedes Alvarez; Fernando Albericio
Journal:  Chem Rev       Date:  2009-06       Impact factor: 60.622

5.  Towards the total chemical synthesis of integral membrane proteins: a general method for the synthesis of hydrophobic peptide-thioester building blocks.

Authors:  Erik C B Johnson; Stephen B H Kent
Journal:  Tetrahedron Lett       Date:  2007-03-05       Impact factor: 2.415

6.  Modification of C-terminal peptides to form peptide enamides: synthesis of chondriamides A and C.

Authors:  X Wang; J A Porco
Journal:  J Org Chem       Date:  2001-11-30       Impact factor: 4.354

7.  Biological activity and metabolic clearance of a recombinant human thyrotropin produced in Chinese hamster ovary cells.

Authors:  N R Thotakura; R K Desai; L G Bates; E S Cole; B M Pratt; B D Weintraub
Journal:  Endocrinology       Date:  1991-01       Impact factor: 4.736

8.  Comparative properties of insulin-like growth factor 1 (IGF-1) and [Gly7D-Ala]IGF-1 prepared by total chemical synthesis.

Authors:  Youhei Sohma; Brad L Pentelute; Jonathan Whittaker; Qin-Xin Hua; Linda J Whittaker; Michael A Weiss; Stephen B H Kent
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

9.  Modular total chemical synthesis of a human immunodeficiency virus type 1 protease.

Authors:  Erik C B Johnson; Enrico Malito; Yuequan Shen; Dan Rich; Wei-Jen Tang; Stephen B H Kent
Journal:  J Am Chem Soc       Date:  2007-08-18       Impact factor: 15.419

10.  Toward fully synthetic homogeneous beta-human follicle-stimulating hormone (beta-hFSH) with a biantennary N-linked dodecasaccharide. synthesis of beta-hFSH with chitobiose units at the natural linkage sites.

Authors:  Pavel Nagorny; Bernhard Fasching; Xuechen Li; Gong Chen; Baptiste Aussedat; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2009-04-29       Impact factor: 15.419

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  2 in total

Review 1.  Oligosaccharide Synthesis and Translational Innovation.

Authors:  Larissa Krasnova; Chi-Huey Wong
Journal:  J Am Chem Soc       Date:  2019-02-18       Impact factor: 15.419

Review 2.  Challenges and Perspectives in Chemical Synthesis of Highly Hydrophobic Peptides.

Authors:  Lena K Mueller; Andreas C Baumruck; Hanna Zhdanova; Alesia A Tietze
Journal:  Front Bioeng Biotechnol       Date:  2020-03-04
  2 in total

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