Synthesis of Curacin A: A Powerful Antimitotic from the Cyanobacterium Lyngbya majuscula

1995 ◽  
Vol 117 (20) ◽  
pp. 5612-5613 ◽  
Author(s):  
James D. White ◽  
Tae-Seong Kim ◽  
Mitch Nambu
Keyword(s):  
Lyngbya Majuscula ◽  
Curacin A

ChemInform Abstract: Synthetic Study on Curacin A: A Novel Antimitotic Agent from the Cyanobacterium Lyngbya majuscula.

ChemInform ◽  
2010 ◽  
Vol 28 (12) ◽  
pp. no-no
Author(s):  
T. ONODA ◽  
R. SHIRAI ◽  
Y. KOISO ◽  
S. IWASAKI
Keyword(s):  
Antimitotic Agent ◽  
Lyngbya Majuscula ◽  
Curacin A

ChemInform Abstract: Absolute Configuration of Curacin A, a Novel Antimitotic Agent from the Tropical Marine Cyanobacterium Lyngbya majuscula.

ChemInform ◽  
2010 ◽  
Vol 26 (26) ◽  
pp. no-no
Author(s):  
D. G. NAGLE ◽  
R. S. GERALDS ◽  
H.-D. YOO ◽  
W. H. GERWICK ◽  
T.-S. KIM ◽  
...  
Keyword(s):  
Absolute Configuration ◽  
Marine Cyanobacterium ◽  
Antimitotic Agent ◽  
Lyngbya Majuscula ◽  
Curacin A

scholarly journals Crystal Structure of the ECH2 Catalytic Domain of CurF from Lyngbya majuscula

2007 ◽  
Vol 282 (49) ◽  
pp. 35954-35963 ◽  
Author(s):  
Todd W. Geders ◽  
Liangcai Gu ◽  
Jonathan C. Mowers ◽  
Haichuan Liu ◽  
William H. Gerwick ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Functional Group ◽  
Catalytic Domain ◽  
Acyl Carrier Protein ◽  
Cyclopropane Ring ◽  
Chemical Diversity ◽  
Site Directed Mutagenesis ◽  
Lyngbya Majuscula ◽  
Multifunctional Protein ◽  
Curacin A

Curacin A is a mixed polyketide/nonribosomal peptide possessing anti-mitotic and anti-proliferative activity. In the biosynthesis of curacin A, the N-terminal domain of the CurF multifunctional protein catalyzes decarboxylation of 3-methylglutaconyl-acyl carrier protein (ACP) to 3-methylcrotonyl-ACP, the postulated precursor of the cyclopropane ring of curacin A. This decarboxylase is encoded within an “HCS cassette” that is used by several other polyketide biosynthetic systems to generate chemical diversity by introduction of a β-branch functional group to the natural product. The crystal structure of the CurF N-terminal ECH2 domain establishes that the protein is a crotonase superfamily member. Ala78 and Gly118 form an oxyanion hole in the active site that includes only three polar side chains as potential catalytic residues. Site-directed mutagenesis and a biochemical assay established critical functions for His240 and Lys86, whereas Tyr82 was nonessential. A decarboxylation mechanism is proposed in which His240 serves to stabilize the substrate carboxylate and Lys86 donates a proton to C-4 of the acyl-ACP enolate intermediate to form the Δ2 unsaturated isopentenoyl-ACP product. The CurF ECH2 domain showed a 20-fold selectivity for ACP-over CoA-linked substrates. Specificity for ACP-linked substrates has not been reported for any other crotonase superfamily decarboxylase. Tyr73 may select against CoA-linked substrates by blocking a contact of Arg38 with the CoA adenosine 5′-phosphate.

Synthesis of curacin A, an antimitotic cyclopropane-thiazoline from the marine cyanobacterium Lyngbya majuscula

1996 ◽  
Vol 37 (40) ◽  
pp. 7167-7170 ◽  
Author(s):  
Jing-Yu Lai ◽  
Jurong Yu ◽  
Belew Mekonnen ◽  
J.R. Falck
Keyword(s):  
Marine Cyanobacterium ◽  
Lyngbya Majuscula ◽  
Curacin A

Structure of Curacin A, a Novel Antimitotic, Antiproliferative and Brine Shrimp Toxic Natural Product from the Marine Cyanobacterium Lyngbya majuscula

1994 ◽  
Vol 59 (6) ◽  
pp. 1243-1245 ◽  
Author(s):  
William H. Gerwick ◽  
Philip J. Proteau ◽  
Dale G. Nagle ◽  
Ernest Hamel ◽  
Andrei Blokhin ◽  
...  
Keyword(s):  
Natural Product ◽  
Brine Shrimp ◽  
Marine Cyanobacterium ◽  
Lyngbya Majuscula ◽  
Curacin A

Synthetic study on curacin A: A novel antimitotic agent from the cyanobacterium Lyngbya majuscula

Tetrahedron ◽  
1996 ◽  
Vol 52 (46) ◽  
pp. 14543-14562 ◽  
Author(s):  
Toshihiko Onoda ◽  
Ryuichi Shirai ◽  
Yukiko Koiso ◽  
Shigeo Iwasaki
Keyword(s):  
Antimitotic Agent ◽  
Lyngbya Majuscula ◽  
Curacin A

Absolute configuration of curacin A, a novel antimitotic agent from the tropical marine cyanobacterium Lyngbya majuscula

1995 ◽  
Vol 36 (8) ◽  
pp. 1189-1192 ◽  
Author(s):  
Dale G. Nagle ◽  
Robin S. Geralds ◽  
Hye-Dong Yoo ◽  
William H. Gerwick ◽  
Tae-Seong Kim ◽  
...  
Keyword(s):  
Absolute Configuration ◽  
Marine Cyanobacterium ◽  
Antimitotic Agent ◽  
Lyngbya Majuscula ◽  
Curacin A
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