Modified Peptides

(1) Methylated/Acetylated Histone
 

We have developed a practical method for a  “one-pot” native chemical ligation of peptide hydrazides that would circumvent  the need for the isolation of the intermediate products. This method employed a  fast and selective arylboronate oxidation reaction mediated by H2O2, which  draws attention to the potential applications of the thus far under-exploited  boron-based functionalities in protein chemical synthesis. Our method have been  applied to a scalable total synthesis of modified histones (with five analogues  of H3 and H4 as examples) on a multi-milligram scale, with good homogeneity.

Scheme 1. Synthesis of full-length ribosomal protein S25 through the ligation of peptide hydrazides


(2) Ubiqutinated Histone


Here we report an alternative strategy for  total chemical synthesis of homogenous histone H2B-K34-ubiquitylation  (H2B-K34Ub) by using acid-cleavable auxiliary-mediated ligation of peptide  hydrazides for site-specific ubiquitylation. Synthetic H2B-K34Ub was  efficiently incorporated into nucleosomes.

Scheme 1. Synthesis of full-length ribosomal protein S25 through the ligation of peptide hydrazides


Reference:

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1. Li, J. et al. One-pot native chemical ligation  of peptide hydrazides enables total synthesis of modified histones. Organic & biomolecular chemistry12, 5435-5441, doi:10.1039/c4ob00715h  (2014).

2. Li, J. et al. Chemical Synthesis of K34-Ubiquitylated H2B for Nucleosome  Reconstitution and Single-Particle Cryo-Electron Microscopy Structural  Analysis. Chembiochem : a European  journal of chemical biology18,  176-180, doi:10.1002/cbic.201600551 (2017).

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