Online citations, reference lists, and bibliographies.
Please confirm you are human
(Sign Up for free to never see this)
← Back to Search

Suzuki–Miyaura Coupling For General Synthesis Of Dehydrocoelenterazine Applicable For 6-position Analogs Directing Toward Bioluminescence Studies

Wong Phakhodee, Mitsuko Toyoda, Chun-ming Chou, Nisachon Khunnawutmanotham, M. Isobe
Published 2011 · Chemistry

Save to my Library
Download PDF
Analyze on Scholarcy
Share
Synthesis of coelenterazine analogs is in recent demand to supply more luminescent compounds with reasonable stability as substrate for the photoprotein manipulated in a living cells or particular organelle. There are limited methods for the synthesis of 6-substituted coelenterazine due to the route and instability of the compounds under the existing conditions. This paper describes six examples including Suzuki–Miyaura cross coupling reaction with reactive triflate (unstable) and stable tosylate intermediates of the imidazo[1,2-a]pyrazin-3-one. Five examples of 2-amino-3-benzyl-5-O-Tf-pyrazine are also discussed. The product coelenterazine analogs are obtained in the form of dehydrocoelenterazine, which is the substrate of a squid photoprotein, symplectin.
This paper references
10.1246/CL.1975.247
THE LIGHT-EMITTER IN BIOLUMINESCENCE OF THE SEA CACTUS CAVERNULARIA OBESA
O. Shimomura (1975)
10.1246/BCSJ.73.465
Synthesis, Chemi- and Bioluminescence Properties, and Photolysis of a Coelenterazine Analogue Having a Photoreactive Azido Group
J. Zheng (2000)
10.1246/CL.1994.843
Photoprotein of Luminous Squid, Symplectoteuthis oualaniensis and Reconstruction of the Luminous System
H. Takahashi (1994)
10.1016/J.TET.2003.08.040
Synthesis of 3,7-dihydroimidazo[1,2a]pyrazine-3-ones and their chemiluminescent properties
M. Adamczyk (2003)
10.1016/S0960-894X(01)80734-4
Symplectoteuthis bioluminescence (1) Structure and binding form of chromophore in photoprotein of a luminous squid
H. Takahashi (1993)
10.1021/JA005663V
Design, synthesis, and evaluation of the transition- state inhibitors of coelenterazine bioluminescence: probing the chiral environment of active site.
H. Nakamura (2001)
10.1016/j.bmcl.2008.08.113
Pholasin luminescence is enhanced by addition of dehydrocoelenterazine.
M. Kuse (2008)
10.1246/BCSJ.63.3132
Synthesis and chemiluminescence of coelenterazine(Oplophorus luciferin) analogues.
K. Teranishi (1990)
10.1039/C39730000492
Chemiluminescence of Renilla(sea pansy) luciferin and its analogues
Kazuo Hori (1973)
10.1016/S0040-4039(00)77172-3
Synthesis of silyl peroxide of coelenterazine (oplophorus luciferin) analogue for precursor of luminescence
K. Teranishi (1994)
10.1017/S0025315400015277
Evidence For De Novo Biosynthesis of Coelenterazine in the Bioluminescent Midwater Shrimp, Systellaspis Debilis C
C. M. Thomson (1995)
IDENTIFICATION OF beta-LIKE ADRENOCEPTORS ASSOCIATED WITH BIOLUMINESCENCE IN THE SEA PANSY RENILLA KOELLIKERI
E. W. Awad (1993)
10.1021/BI00599A008
Properties and reaction mechanism of the bioluminescence system of the deep-sea shrimp Oplophorus gracilorostris.
O. Shimomura (1978)
10.1081/SCC-120013744
A CONVENIENT METHOD FOR THE PREPARATION OF α-KETOACETALS
M. Adamczyk (2002)
10.1016/S0040-4020(00)00163-0
Synthesis of 13C-Dehydrocoelenterazine and NMR Studies on the Bioluminescence of a Symplectoteuthis Model
M. Kuse (2000)
10.1016/S0040-4039(01)85503-9
Squid bioluminescence III. Isolation and structure of Watasenia luciferin
S. Inoue (1976)
10.1039/C39760001056
Oplophorus luciferin, bioluminescent substance of the decapod shrimps, Oplophorus spinosus and Heterocarpus laevigatus
S. Inoue (1976)
10.1016/j.bbagen.2008.01.016
Bioluminescence of the arm light organs of the luminous squid Watasenia scintillans.
K. Teranishi (2008)
10.1016/0305-0491(80)90044-9
Widespread occurrence of coelenterazine in marine bioluminescence
O. Shimomura (1980)
10.1073/PNAS.70.1.120
Structure and chemical synthesis of a biologically active form of renilla (sea pansy) luciferin.
K. Hori (1973)
10.1016/S0960-894X(98)00525-3
Synthesis of 13C-dehydrocoelenterazine and model studies on Symplectoteuthis squid bioluminescence.
M. Isobe (1998)
10.1016/j.bbrc.2009.10.028
Biosynthesis of coelenterazine in the deep-sea copepod, Metridia pacifica.
Y. Oba (2009)
10.1016/j.febslet.2009.04.043
The intrinsic fluorescence of apo‐obelin and apo‐aequorin and use of its quenching to characterize coelenterazine binding
E. Eremeeva (2009)
10.1039/C39940002405
Synthesis and preliminary chemie- and bio-iuminescence studies of a novel photolabile coelenterazine analogue with a trifluoromethyl diazirine group
F. Chen (1994)
10.1246/BCSJ.82.870
Substituent Effect of Imino-O-arenesulfonates, a Coupling Partner in Suzuki-Miyaura Reaction for Substitution of the Pyrazine Ring : A Study for the Synthesis of Coelenterazine Analogs
A. Makarasen (2009)
10.1016/S0006-291X(02)00296-6
A novel photoprotein from oceanic squid (Symplectoteuthis oualaniensis) with sequence similarity to mammalian carbon-nitrogen hydrolase domains.
T. Fujii (2002)
10.1093/PCP/PCE150
Sugar-induced increase in cytosolic Ca(2+) in Arabidopsis thaliana whole plants.
T. Furuichi (2001)
10.1016/S0040-4039(01)00340-9
Chemi- and bioluminescence of coelenterazine analogues with a conjugated group at the C-8 position
C. Wu (2001)
10.1016/S0040-4039(01)92245-2
Squid bioluminescence I. Structure of oxyluciferin, a possible light-emitter in the bioluminescence of
T. Goto (1974)
10.1021/ol901275n
Regio- and chemoselective multiple functionalization of chloropyrazine derivatives. Application to the synthesis of coelenterazine.
M. Mosrin (2009)
10.1016/S0005-2736(02)00447-9
Bioluminescence reaction catalyzed by membrane-bound luciferase in the "firefly squid," Watasenia scintillans.
F. Tsuji (2002)
10.1073/PNAS.75.6.2611
Peroxidized coelenterazine, the active group in the photoprotein aequorin.
O. Shimomura (1978)
10.1016/J.TET.2003.11.052
Novel synthetic route of aryl-aminopyrazine
M. Kuse (2004)
10.2183/PJAB.84.386
Cysteine-390 is the binding site of luminous substance with symplectin, a photoprotein from Okinawan squid, Symplectoteuthis oualaniensis.
M. Isobe (2008)



This paper is referenced by
10.1038/s41598-017-00955-6
Luciferase-Specific Coelenterazine Analogues for Optical Contamination-Free Bioassays
Ryo Nishihara (2017)
10.1016/B978-0-08-096807-0.00013-0
Six-Membered Ring Systems
L. Yet (2012)
10.1007/978-1-4939-3813-1_2
Synthetic Bioluminescent Coelenterazine Derivatives.
Ryo Nishihara (2016)
10.1039/c3ob40460a
Transition metal-catalyzed functionalization of pyrazines.
N. Nikishkin (2013)
10.1016/J.DYEPIG.2016.10.021
Luminescent tetrahydrodibenzo[a,i]phenanthridin-5-yl)phenol-boron complexes (borophenanthridines)
B. Umamahesh (2017)
10.1002/asia.201100089
Dynamic chirality determines critical roles for bioluminescence in symplectin-dehydrocoelenterazine system.
V. Kongjinda (2011)
10.1016/J.TET.2015.09.048
Multicomponent synthesis of novel coelenterazine derivatives substituted at the C-3 position
V. Vece (2015)
10.3987/COM-12-S(N)85
CHEMICAL SYNTHESIS OF COELENTERAZINE AND ITS ANALOGS : NEW ROUTE TOWARD FOUR SEGMENT-COUPLINGS (Dedicated to Professor Dr. Ei-ichi Negishi on the occasion of his 77th birthday)
Chun-ming Chou (2012)
10.1039/c2ob25787d
Palladium-catalyzed cross-coupling of various phosphorus pronucleophiles with chloropyrazines: synthesis of novel Am(III)-selective extractants.
N. Nikishkin (2012)
10.1007/s12039-013-0561-0
Silica-acac-supported palladium nanoparticles as an efficient and reusable heterogeneous catalyst in the Suzuki–Miyaura cross-coupling reaction in water
A. Hajipour (2014)
10.1002/EJOC.201101783
Suzuki–Miyaura Cross‐Coupling Reactions in a Solkane365/227/Ethanol Blend at Ambient Temperature
X. Xu (2012)
10.1016/j.bmc.2014.05.044
Molecular mechanism of Symplectoteuthis bioluminescence--part 4: chromophore exchange and oxidation of the cysteine residue.
Chun-ming Chou (2014)
10.1016/J.TETLET.2011.11.053
Suzuki-Miyaura cross-coupling of aryldiazonium silica sulfates under mild and heterogeneous conditions
A. Zarei (2012)
10.1002/chem.201501531
Synthetic Routes to Coelenterazine and Other Imidazo[1,2-a]pyrazin-3-one Luciferins: Essential Tools for Bioluminescence-Based Investigations.
Eloi P. Coutant (2015)
Semantic Scholar Logo Some data provided by SemanticScholar