Study of the Paternò–Büchi type photolabile protecting group and application to various acids

Youlai Zhang; Huan Zhang; Chi Ma; Junru Li; Yasuhiro Nishiyama; Hiroki Tanimoto; Tsumoru Morimoto; Kiyomi Kakiuchi

doi:10.1016/j.tetlet.2016.09.065

Study of the Paternò–Büchi type photolabile protecting group and application to various acids

Youlai Zhang, Huan Zhang^*, Chi Ma, Junru Li, Yasuhiro Nishiyama, Hiroki Tanimoto, Tsumoru Morimoto, Kiyomi Kakiuchi

^*Corresponding author for this work

Biorecognition Chemistry

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

12 Scopus citations

Abstract

An efficient photolabile protecting group, thiochromone S,S-dioxides with the diazomethyl group for phosphate derivatives, amino acids and sulfonic acids was developed. Protection and photodeprotection reactions proceeded smoothly under mild conditions without any catalyst.¹H NMR and HPLC spectra studies demonstrated the photolysis properties of the photolabile protecting group and gave an exact quantification of the released substrates. Specially, the photoproduct derived from the thiochromone derivatives following Paternò–Büchi type photo-cycloaddition showed high fluorescence intensity. This fluorescent characteristic demonstrated the photodeprotection progress also can be monitored by fluorescence spectra.

Original language	English
Pages (from-to)	5179-5184
Number of pages	6
Journal	Tetrahedron Letters
Volume	57
Issue number	47
DOIs	https://doi.org/10.1016/j.tetlet.2016.09.065
State	Published - 2016

Keywords

Amino acids
Photochemistry
Photolabile protecting group
Sulfonic acids
Thiochromone

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2016.09.065

Cite this

@article{f20d19e9ca3943dd89bd2039bc3d4596,

title = "Study of the Patern{\`o}–B{\"u}chi type photolabile protecting group and application to various acids",

abstract = "An efficient photolabile protecting group, thiochromone S,S-dioxides with the diazomethyl group for phosphate derivatives, amino acids and sulfonic acids was developed. Protection and photodeprotection reactions proceeded smoothly under mild conditions without any catalyst.1H NMR and HPLC spectra studies demonstrated the photolysis properties of the photolabile protecting group and gave an exact quantification of the released substrates. Specially, the photoproduct derived from the thiochromone derivatives following Patern{\`o}–B{\"u}chi type photo-cycloaddition showed high fluorescence intensity. This fluorescent characteristic demonstrated the photodeprotection progress also can be monitored by fluorescence spectra.",

keywords = "Amino acids, Photochemistry, Photolabile protecting group, Sulfonic acids, Thiochromone",

author = "Youlai Zhang and Huan Zhang and Chi Ma and Junru Li and Yasuhiro Nishiyama and Hiroki Tanimoto and Tsumoru Morimoto and Kiyomi Kakiuchi",

note = "Publisher Copyright: {\textcopyright} 2016",

year = "2016",

doi = "10.1016/j.tetlet.2016.09.065",

language = "英語",

volume = "57",

pages = "5179--5184",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "47",

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TY - JOUR

T1 - Study of the Paternò–Büchi type photolabile protecting group and application to various acids

AU - Zhang, Youlai

AU - Zhang, Huan

AU - Ma, Chi

AU - Li, Junru

AU - Nishiyama, Yasuhiro

AU - Tanimoto, Hiroki

AU - Morimoto, Tsumoru

AU - Kakiuchi, Kiyomi

PY - 2016

Y1 - 2016

N2 - An efficient photolabile protecting group, thiochromone S,S-dioxides with the diazomethyl group for phosphate derivatives, amino acids and sulfonic acids was developed. Protection and photodeprotection reactions proceeded smoothly under mild conditions without any catalyst.1H NMR and HPLC spectra studies demonstrated the photolysis properties of the photolabile protecting group and gave an exact quantification of the released substrates. Specially, the photoproduct derived from the thiochromone derivatives following Paternò–Büchi type photo-cycloaddition showed high fluorescence intensity. This fluorescent characteristic demonstrated the photodeprotection progress also can be monitored by fluorescence spectra.

AB - An efficient photolabile protecting group, thiochromone S,S-dioxides with the diazomethyl group for phosphate derivatives, amino acids and sulfonic acids was developed. Protection and photodeprotection reactions proceeded smoothly under mild conditions without any catalyst.1H NMR and HPLC spectra studies demonstrated the photolysis properties of the photolabile protecting group and gave an exact quantification of the released substrates. Specially, the photoproduct derived from the thiochromone derivatives following Paternò–Büchi type photo-cycloaddition showed high fluorescence intensity. This fluorescent characteristic demonstrated the photodeprotection progress also can be monitored by fluorescence spectra.

KW - Amino acids

KW - Photochemistry

KW - Photolabile protecting group

KW - Sulfonic acids

KW - Thiochromone

UR - http://www.scopus.com/inward/record.url?scp=84994223667&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2016.09.065

DO - 10.1016/j.tetlet.2016.09.065

M3 - 学術論文

AN - SCOPUS:84994223667

SN - 0040-4039

VL - 57

SP - 5179

EP - 5184

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 47

ER -

Study of the Paternò–Büchi type photolabile protecting group and application to various acids

Abstract

Keywords

ASJC Scopus subject areas

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