Development of a luminescence-controllable firefly luciferin analogue using selective enzymatic cyclization

Shuji Ioka; Tsuyoshi Saitoh; Shojiro A. Maki; Masaya Imoto; Shigeru Nishiyama

doi:10.1016/j.tet.2016.09.069

Development of a luminescence-controllable firefly luciferin analogue using selective enzymatic cyclization

Shuji Ioka
, Tsuyoshi Saitoh
, Shojiro A. Maki
, Masaya Imoto
, Shigeru Nishiyama

Department of Biosciences and Informatics

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

4 Citations (Scopus)

Abstract

In this study, a new firefly luciferin analog that can switch firefly bioluminescence (BL) activity from ‘off’ to ‘on’ state was designed and synthesized. BL inactive N-Ac-γ-glutamate luciferin 3 contains an acyclic precursor of the thiazoline moiety. Enzymatic treatment of 3 with aminoacylase resulted in a smooth removal of the acyl protecting group and concomitant cyclization to provide BL active carboluciferin 2.

Original language	English
Pages (from-to)	7505-7508
Number of pages	4
Journal	Tetrahedron
Volume	72
Issue number	47
DOIs	https://doi.org/10.1016/j.tet.2016.09.069
Publication status	Published - 2016

Keywords

Bioluminescence
Enzyme detection
Firefly luciferase
Firefly luciferin derivative
Organic synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2016.09.069

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title = "Development of a luminescence-controllable firefly luciferin analogue using selective enzymatic cyclization",

abstract = "In this study, a new firefly luciferin analog that can switch firefly bioluminescence (BL) activity from {\textquoteleft}off{\textquoteright} to {\textquoteleft}on{\textquoteright} state was designed and synthesized. BL inactive N-Ac-γ-glutamate luciferin 3 contains an acyclic precursor of the thiazoline moiety. Enzymatic treatment of 3 with aminoacylase resulted in a smooth removal of the acyl protecting group and concomitant cyclization to provide BL active carboluciferin 2.",

keywords = "Bioluminescence, Enzyme detection, Firefly luciferase, Firefly luciferin derivative, Organic synthesis",

author = "Shuji Ioka and Tsuyoshi Saitoh and Maki, \{Shojiro A.\} and Masaya Imoto and Shigeru Nishiyama",

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

year = "2016",

doi = "10.1016/j.tet.2016.09.069",

language = "English",

volume = "72",

pages = "7505--7508",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "47",

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TY - JOUR

T1 - Development of a luminescence-controllable firefly luciferin analogue using selective enzymatic cyclization

AU - Ioka, Shuji

AU - Saitoh, Tsuyoshi

AU - Maki, Shojiro A.

AU - Imoto, Masaya

AU - Nishiyama, Shigeru

PY - 2016

Y1 - 2016

N2 - In this study, a new firefly luciferin analog that can switch firefly bioluminescence (BL) activity from ‘off’ to ‘on’ state was designed and synthesized. BL inactive N-Ac-γ-glutamate luciferin 3 contains an acyclic precursor of the thiazoline moiety. Enzymatic treatment of 3 with aminoacylase resulted in a smooth removal of the acyl protecting group and concomitant cyclization to provide BL active carboluciferin 2.

AB - In this study, a new firefly luciferin analog that can switch firefly bioluminescence (BL) activity from ‘off’ to ‘on’ state was designed and synthesized. BL inactive N-Ac-γ-glutamate luciferin 3 contains an acyclic precursor of the thiazoline moiety. Enzymatic treatment of 3 with aminoacylase resulted in a smooth removal of the acyl protecting group and concomitant cyclization to provide BL active carboluciferin 2.

KW - Bioluminescence

KW - Enzyme detection

KW - Firefly luciferase

KW - Firefly luciferin derivative

KW - Organic synthesis

UR - https://www.scopus.com/pages/publications/84992223533

UR - https://www.scopus.com/pages/publications/84992223533#tab=citedBy

U2 - 10.1016/j.tet.2016.09.069

DO - 10.1016/j.tet.2016.09.069

M3 - Article

AN - SCOPUS:84992223533

SN - 0040-4020

VL - 72

SP - 7505

EP - 7508

JO - Tetrahedron

JF - Tetrahedron

IS - 47

ER -

Development of a luminescence-controllable firefly luciferin analogue using selective enzymatic cyclization

Abstract

Keywords

ASJC Scopus subject areas

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