Oxidative peptide bond formation of glycine-amino acid using 2-(aminomethyl)malononitrile as a glycine unit

Xiaoling Wang; Jing Li; Yujiro Hayashi

doi:10.1039/d1cc00130b

Oxidative peptide bond formation of glycine-amino acid using 2-(aminomethyl)malononitrile as a glycine unit

Xiaoling Wang, Jing Li, Yujiro Hayashi

SCI - Chemistry

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

Abstract

Amide linkage of glycine-amino acid was synthesized by coupling of substituted 2-(aminomethyl)malononitrile as a C-terminal glycine unit and N-terminal amine using CsOAc and O₂in an aqueous solution. This is a coupling reagent-free and catalyst-free peptide synthesisviaoxidative amide bond formation. Various tripeptides and tetrapeptides were synthesized efficiently and the sulfide moiety is inert even under an oxygen atmosphere.

Original language	English
Pages (from-to)	4283-4286
Number of pages	4
Journal	Chemical Communications
Volume	57
Issue number	35
DOIs	https://doi.org/10.1039/d1cc00130b
Publication status	Published - 2021 May 2

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

Access to Document

10.1039/d1cc00130b

Cite this

@article{117c60e804c4459bb7fc86404f51f0fc,

title = "Oxidative peptide bond formation of glycine-amino acid using 2-(aminomethyl)malononitrile as a glycine unit",

abstract = "Amide linkage of glycine-amino acid was synthesized by coupling of substituted 2-(aminomethyl)malononitrile as a C-terminal glycine unit and N-terminal amine using CsOAc and O2in an aqueous solution. This is a coupling reagent-free and catalyst-free peptide synthesisviaoxidative amide bond formation. Various tripeptides and tetrapeptides were synthesized efficiently and the sulfide moiety is inert even under an oxygen atmosphere.",

author = "Xiaoling Wang and Jing Li and Yujiro Hayashi",

note = "Funding Information: This work was supported by JSPS KAKENHI JP19H05630 and JP20H04801. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2021.",

year = "2021",

month = may,

day = "2",

doi = "10.1039/d1cc00130b",

language = "English",

volume = "57",

pages = "4283--4286",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "35",

}

TY - JOUR

T1 - Oxidative peptide bond formation of glycine-amino acid using 2-(aminomethyl)malononitrile as a glycine unit

AU - Wang, Xiaoling

AU - Li, Jing

AU - Hayashi, Yujiro

N1 - Funding Information: This work was supported by JSPS KAKENHI JP19H05630 and JP20H04801. Publisher Copyright: © The Royal Society of Chemistry 2021.

PY - 2021/5/2

Y1 - 2021/5/2

N2 - Amide linkage of glycine-amino acid was synthesized by coupling of substituted 2-(aminomethyl)malononitrile as a C-terminal glycine unit and N-terminal amine using CsOAc and O2in an aqueous solution. This is a coupling reagent-free and catalyst-free peptide synthesisviaoxidative amide bond formation. Various tripeptides and tetrapeptides were synthesized efficiently and the sulfide moiety is inert even under an oxygen atmosphere.

AB - Amide linkage of glycine-amino acid was synthesized by coupling of substituted 2-(aminomethyl)malononitrile as a C-terminal glycine unit and N-terminal amine using CsOAc and O2in an aqueous solution. This is a coupling reagent-free and catalyst-free peptide synthesisviaoxidative amide bond formation. Various tripeptides and tetrapeptides were synthesized efficiently and the sulfide moiety is inert even under an oxygen atmosphere.

UR - http://www.scopus.com/inward/record.url?scp=85104989256&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85104989256&partnerID=8YFLogxK

U2 - 10.1039/d1cc00130b

DO - 10.1039/d1cc00130b

M3 - Article

C2 - 33913954

AN - SCOPUS:85104989256

VL - 57

SP - 4283

EP - 4286

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

IS - 35

ER -

Oxidative peptide bond formation of glycine-amino acid using 2-(aminomethyl)malononitrile as a glycine unit

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this