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Peptide late-stage C(sp³)-H arylation by native asparagine assistance without exogenous directing groups.

ABSTRACT: There is a strong demand for novel native peptide motifs for post-synthetic modifications of peptides without pre-installation and subsequent removal of directing groups. Herein, we report an efficient method for peptide late-stage C(sp³)-H arylations assisted by the unmodified side chain of asparagine (Asn) without any exogenous directing group. Thereby, site-selective arylations of C(sp³)-H bonds at the N-terminus of di-, tri-, and tetrapeptides have been achieved. Likewise, we have constructed a key building block for accessing agouti-related protein (AGRP) active loop analogues in a concise manner.

SUBMITTER: Weng Y

PROVIDER: S-EPMC8161531 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature

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Peptide late-stage C(sp3)-H arylation by native asparagine assistance without exogenous directing groups.

Weng Yiyi Y Ding Xingxing X Oliveira João C A JCA Xu Xiaobin X Kaplaneris Nikolaos N Zhu Meijie M Chen Hantao H Chen Zhuo Z Ackermann Lutz L

Chemical science 20200812 34

There is a strong demand for novel native peptide motifs for post-synthetic modifications of peptides without pre-installation and subsequent removal of directing groups. Herein, we report an efficient method for peptide late-stage C(sp3)-H arylations assisted by the unmodified side chain of asparagine (Asn) without any exogenous directing group. Thereby, site-selective arylations of C(sp3)-H bonds at the N-terminus of di-, tri-, and tetrapeptides have been achieved. Likewi ...[more]

PMID: 34094199

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