title: Peptide o-aminoanilides as crypto-thioesters for protein chemical synthesis.
abstract: Fully unprotected peptide o-aminoanilides can be efficiently activated by NaNO2 in aqueous solution to furnish peptide thioesters for use in native chemical ligation. This finding enables the convergent synthesis of proteins from readily synthesizable peptide o-aminoanilides as a new type of crypto-thioesters. The practicality of this approach is shown by the synthesis of histone H2B from five peptide segments. Purification or solubilization tags, which are sometimes needed to improve the efficiency of protein chemical synthesis, can be incorporated into the o-aminoanilide moiety, as demonstrated in the preparation of the cyclic protein lactocyclicin Q.
authors.affiliation: Tsinghua-Peking Center for Life Sciences, Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084 (China).
authors.forename: Jia-Xing
authors.initials: JX
authors.lastname: Wang
authors.forename: Ge-Min
authors.initials: GM
authors.lastname: Fang
authors.forename: Yao
authors.initials: Y
authors.lastname: He
authors.forename: Da-Liang
authors.initials: DL
authors.lastname: Qu
authors.forename: Min
authors.initials: M
authors.lastname: Yu
authors.forename: Zhang-Yong
authors.initials: ZY
authors.lastname: Hong
authors.forename: Lei
authors.initials: L
authors.lastname: Liu
mesh_terms: D000586:Amination; D000595:Amino Acid Sequence; D000813:Anilides / Q000138:chemical synthesis / Q000737:chemistry*; D004952:Esters; D006657:Histones / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008969:Molecular Sequence Data; D009584:Nitrogen / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000813:Anilides; D004952:Esters; D006657:Histones; D010455:Peptides; D013438:Sulfhydryl Compounds; C003320:sodium nitride; D009584:Nitrogen
keywords: native chemical ligation; peptide o-aminoanilides; peptide thioesters; proteins; sodium nitrite