Abstract
Novel click chemistry was developed based on the biosynthetic process of firefly luciferin, which includes an ideal coupling of a cyanothiazole residue with cysteine. Among various biomimetic couplings of nitriles with cysteine derivatives, the approach using 4-cyanopyridine and cysteine methyl ester provided a very rapid and quantitative conversion to the corresponding thiazole without any metal catalyst at room temperature.
| Original language | English |
|---|---|
| Pages (from-to) | 753-755 |
| Number of pages | 3 |
| Journal | Chemistry Letters |
| Volume | 46 |
| Issue number | 5 |
| DOIs | |
| Publication status | Published - 2017 |
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Keywords
- Biomimetic coupling
- Click chemistry
- Firefly luciferin
ASJC Scopus subject areas
- Chemistry(all)
Cite this
Click reaction based on the biosynthesis of firefly luciferin. / Toyama, Tomohisa; Saitoh, Tsuyoshi; Takahashi, Yuka; Oka, Kotaro; Citterio, Daniel; Suzuki, Koji; Nishiyama, Shigeru.
In: Chemistry Letters, Vol. 46, No. 5, 2017, p. 753-755.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Click reaction based on the biosynthesis of firefly luciferin
AU - Toyama, Tomohisa
AU - Saitoh, Tsuyoshi
AU - Takahashi, Yuka
AU - Oka, Kotaro
AU - Citterio, Daniel
AU - Suzuki, Koji
AU - Nishiyama, Shigeru
PY - 2017
Y1 - 2017
N2 - Novel click chemistry was developed based on the biosynthetic process of firefly luciferin, which includes an ideal coupling of a cyanothiazole residue with cysteine. Among various biomimetic couplings of nitriles with cysteine derivatives, the approach using 4-cyanopyridine and cysteine methyl ester provided a very rapid and quantitative conversion to the corresponding thiazole without any metal catalyst at room temperature.
AB - Novel click chemistry was developed based on the biosynthetic process of firefly luciferin, which includes an ideal coupling of a cyanothiazole residue with cysteine. Among various biomimetic couplings of nitriles with cysteine derivatives, the approach using 4-cyanopyridine and cysteine methyl ester provided a very rapid and quantitative conversion to the corresponding thiazole without any metal catalyst at room temperature.
KW - Biomimetic coupling
KW - Click chemistry
KW - Firefly luciferin
UR - http://www.scopus.com/inward/record.url?scp=85028083783&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85028083783&partnerID=8YFLogxK
U2 - 10.1246/cl.170094
DO - 10.1246/cl.170094
M3 - Article
VL - 46
SP - 753
EP - 755
JO - Chemistry Letters
JF - Chemistry Letters
SN - 0366-7022
IS - 5
ER -