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Literature DB >> 23569249

Protein chemical synthesis by serine and threonine ligation.

Yinfeng Zhang¹, Ci Xu, Hiu Yung Lam, Chi Lung Lee, Xuechen Li.

Abstract

An efficient method has been developed for the salicylaldehyde ester-mediated ligation of unprotected peptides at serine (Ser) or threonine (Thr) residues. The utility of this peptide ligation approach has been demonstrated through the convergent syntheses of two therapeutic peptides--ovine-corticoliberin and Forteo--and the human erythrocyte acylphosphatase protein (∼11 kDa). The requisite peptide salicylaldehyde ester precursor is prepared in an epimerization-free manner via Fmoc-solid-phase peptide synthesis.

Entities: Chemical Gene Species

Mesh：

Substances：

Year: 2013 PMID： 23569249 PMCID： PMC3637748 DOI： 10.1073/pnas.1221012110

Source DB: PubMed Journal: Proc Natl Acad Sci U S A ISSN： 0027-8424 Impact factor: 11.205

38 in total

1. Chemical synthesis of homogeneous human glycosyl-interferon-β that exhibits potent antitumor activity in vivo.

Authors: Izumi Sakamoto; Katsunari Tezuka; Kazuhiro Fukae; Kazuyuki Ishii; Keisuke Taduru; Masatoshi Maeda; Masaki Ouchi; Kenta Yoshida; Yuri Nambu; Jun Igarashi; Naohiro Hayashi; Takashi Tsuji; Yasuhiro Kajihara
Journal: J Am Chem Soc Date: 2012-03-15 Impact factor: 15.419

2. Free-radical-based, specific desulfurization of cysteine: a powerful advance in the synthesis of polypeptides and glycopolypeptides.

Authors: Qian Wan; Samuel J Danishefsky
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

Review 3. Glycoprotein synthesis: an update.

Authors: David P Gamblin; Eoin M Scanlan; Benjamin G Davis
Journal: Chem Rev Date: 2009-01 Impact factor: 60.622

4. Application of the logic of cysteine-free native chemical ligation to the synthesis of Human Parathyroid Hormone (hPTH).

Authors: Shiying Shang; Zhongping Tan; Samuel J Danishefsky
Journal: Proc Natl Acad Sci U S A Date: 2011-03-28 Impact factor: 11.205

5. Salicylaldehyde ester-induced chemoselective peptide ligations: enabling generation of natural peptidic linkages at the serine/threonine sites.

Authors: Xuechen Li; Hiu Yung Lam; Yinfeng Zhang; Chun Kei Chan
Journal: Org Lett Date: 2010-04-16 Impact factor: 6.005

6. Preparation of protected peptidyl thioester intermediates for native chemical ligation by Nalpha-9-fluorenylmethoxycarbonyl (Fmoc) chemistry: considerations of side-chain and backbone anchoring strategies, and compatible protection for N-terminal cysteine.

Authors: C M Gross; D Lelièvre; C K Woodward; G Barany
Journal: J Pept Res Date: 2005-03

7. 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

8. Amino acid and peptide synthesis and functionalization by the reaction of thioacids with 2,4-dinitrobenzenesulfonamides.

Authors: David Crich; Kasinath Sana; Songpo Guo
Journal: Org Lett Date: 2007-09-27 Impact factor: 6.005

9. The reaction of thio acids with azides: a new mechanism and new synthetic applications.

Authors: Ning Shangguan; Sreenivas Katukojvala; Rachel Greenberg; Lawrence J Williams
Journal: J Am Chem Soc Date: 2003-07-02 Impact factor: 15.419

10. Chemical synthesis of a glycoprotein having an intact human complex-type sialyloligosaccharide under the Boc and Fmoc synthetic strategies.

Authors: Naoki Yamamoto; Yasutaka Tanabe; Ryo Okamoto; Philip E Dawson; Yasuhiro Kajihara
Journal: J Am Chem Soc Date: 2007-12-18 Impact factor: 15.419

35 in total

Review 1. Expanding the chemical toolbox for the synthesis of large and uniquely modified proteins.

Authors: Somasekhar Bondalapati; Muhammad Jbara; Ashraf Brik
Journal: Nat Chem Date: 2016-04-22 Impact factor: 24.427

2. Total Synthesis of Malacidin A by β-Hydroxyaspartic Acid Ligation-Mediated Cyclization and Absolute Structure Establishment.

Authors: Zhenquan Sun; Zhuo Shang; Nicholas Forelli; Kathy Hiu Laam Po; Sheng Chen; Sean F Brady; Xuechen Li
Journal: Angew Chem Int Ed Engl Date: 2020-08-31 Impact factor: 15.336

3. Total synthesis of fellutamides, lipopeptide proteasome inhibitors. More sustainable peptide bond formation.

Authors: Michael C Pirrung; Fa Zhang; Sudhakar Ambadi; Y Gangadhara Rao
Journal: Org Biomol Chem Date: 2016-08-17 Impact factor: 3.876

4. Fully Synthetic Granulocyte Colony-Stimulating Factor Enabled by Isonitrile-Mediated Coupling of Large, Side-Chain-Unprotected Peptides.

Authors: Andrew G Roberts; Eric V Johnston; Jae-Hung Shieh; Joseph P Sondey; Ronald C Hendrickson; Malcolm A S Moore; Samuel J Danishefsky
Journal: J Am Chem Soc Date: 2015-10-01 Impact factor: 15.419