Literature DB >> 25860514

Regioselective formation of multiple disulfide bonds with the aid of postsynthetic S-tritylation.

Masayoshi Mochizuki1, Shugo Tsuda1, Kyoko Tanimura1, Yuji Nishiuchi1,2.   

Abstract

Disulfide bond formation performed in solution with the tert-butylthio (StBu) group was accomplished using a free peptide having only the sulfhydryl groups of Cys protected with the aid of postsynthetic S-tritylation. This facilitated removal of the StBu group with subsequent disulfide formation without any difficulty. This strategy using the StBu group in combination with the widely used acetamidomethyl (Acm), 4-methylbenzyl/4-methoxybenzyl (Meb/Mob), and trityl (Trt) groups enables reliable and regioselective synthesis of multicystine peptides.

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Year:  2015        PMID： 25860514     DOI： 10.1021/acs.orglett.5b00786

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  7 in total

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2.  Coagulation Factor XIIIa Inhibitor Tridegin: On the Role of Disulfide Bonds for Folding, Stability, and Function.

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3.  Direct palladium-mediated on-resin disulfide formation from Allocam protected peptides.

Authors:  Thilini D Kondasinghe; Hasina Y Saraha; Samantha B Odeesho; Jennifer L Stockdill
Journal:  Org Biomol Chem       Date:  2017-04-05       Impact factor: 3.876

4.  Synthesis and Structure Determination of µ-Conotoxin PIIIA Isomers with Different Disulfide Connectivities.

Authors:  Pascal Heimer; Thomas Schmitz; Charlotte A Bäuml; Diana Imhof
Journal:  J Vis Exp       Date:  2018-10-02       Impact factor: 1.355

5.  Chemical and Enzymatic Synthesis of Sialylated Glycoforms of Human Erythropoietin.

Authors:  Hendrik Hessefort; Angelina Gross; Simone Seeleithner; Markus Hessefort; Tanja Kirsch; Lukas Perkams; Klaus Ole Bundgaard; Karen Gottwald; David Rau; Christopher Günther Franz Graf; Elisabeth Rozanski; Sascha Weidler; Carlo Unverzagt
Journal:  Angew Chem Int Ed Engl       Date:  2021-11-02       Impact factor: 16.823

6.  On-Demand Detachment of Succinimides on Cysteine to Facilitate (Semi)Synthesis of Challenging Proteins.

Authors:  Ganga B Vamisetti; Gandhesiri Satish; Prasad Sulkshane; Guy Mann; Michael H Glickman; Ashraf Brik
Journal:  J Am Chem Soc       Date:  2020-11-02       Impact factor: 15.419

7.  Multilayer 3D Chirality and Its Synthetic Assembly.

Authors:  Guanzhao Wu; Yangxue Liu; Zhen Yang; Nandakumar Katakam; Hossein Rouh; Sultan Ahmed; Daniel Unruh; Kazimierz Surowiec; Guigen Li
Journal:  Research (Wash D C)       Date:  2019-06-27
  7 in total

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