New tricyclic geldanamycin analogues from an engineered strain of Streptomyces hygroscopicus JCM4427
作者： Seong Su Hong , Xing Fu Cai , Bang Yeon Hwang , Hong Sub Lee , Bao-Ning Su
DOI: 10.1016/J.TETLET.2009.11.018
关键词: Alkylation 、 Streptomyces hygroscopicus 、 Chemistry 、 Geldanamycin 、 Stereochemistry 、 Mutagenesis 、 Polyketide synthase 、 Double bond 、 Mutant 、 Electrophilic addition
摘要: Abstract Two tricyclic geldanamycin analogues, DHQ5 ( 1 ) and DHQ6 2 ), were produced by a combinatorial mutant (AC15) contained site-directed mutagenesis on the polyketide synthase (PKS) gene with inactivation of post-PKS tailoring genes gel7 Streptomyces hygroscopicus JCM4427. The structural diversity analogues is due to formation unusual additional rings, which are formed alkylation C-21 position C-12 in electrophilic addition C-15 hydroxyl group double bond (C-8–C-9), leads migration (to C-7–C-8) elimination carbamoyloxy ).
elsevier.com
kribb.re.kr参考文章(13)
D Mahalingam, R Swords, J S Carew, S T Nawrocki, K Bhalla, F J Giles, Targeting HSP90 for cancer therapy British Journal of Cancer. ,vol. 100, pp. 1523- 1529 ,(2009) , 10.1038/SJ.BJC.6605066
Tony Taldone, Alexander Gozman, Ronnie Maharaj, Gabriela Chiosis, Targeting Hsp90: small-molecule inhibitors and their clinical development Current Opinion in Pharmacology. ,vol. 8, pp. 370- 374 ,(2008) , 10.1016/J.COPH.2008.06.015
Andreas Rascher, Zhihao Hu, Nina Viswanathan, Andreas Schirmer, Ralph Reid, William C Nierman, Matthew Lewis, C.Richard Hutchinson, Cloning and characterization of a gene cluster for geldanamycin production inStreptomyces hygroscopicusNRRL 3602 FEMS Microbiology Letters. ,vol. 218, pp. 223- 230 ,(2003) , 10.1016/S0378-1097(02)01148-5
Woncheol Kim, Jong Suk Lee, Dongho Lee, Xing Fu Cai, Jin Chul Shin, Kyeong Lee, Choong-Hwan Lee, Sangryeol Ryu, Sang-Gi Paik, Jung Joon Lee, Young-Soo Hong, Mutasynthesis of Geldanamycin by the Disruption of a Gene Producing Starter Unit: Generation of Structural Diversity at the Benzoquinone Ring ChemBioChem. ,vol. 8, pp. 1491- 1494 ,(2007) , 10.1002/CBIC.200700196
Young-Soo Hong, Dongho Lee, Woncheol Kim, Jae-Kap Jeong, Chun-Gyu Kim, Jae Kyung Sohng, Jeong-Hyung Lee, Sang-Gi Paik, Jung Joon Lee, Inactivation of the carbamoyltransferase gene refines post-polyketide synthase modification steps in the biosynthesis of the antitumor agent geldanamycin. Journal of the American Chemical Society. ,vol. 126, pp. 11142- 11143 ,(2004) , 10.1021/JA047769M
Kyeong Lee, Jung S Ryu, Yinglan Jin, Woncheol Kim, Navneet Kaur, Sang J Chung, Yong-Jin Jeon, Joon-Tae Park, Ji S Bang, Hong S Lee, Tae Y Kim, Jung J Lee, Young-Soo Hong, None, Synthesis and anticancer activity of geldanamycin derivatives derived from biosynthetically generated metabolites Organic and Biomolecular Chemistry. ,vol. 6, pp. 340- 348 ,(2008) , 10.1039/B713407J
Woncheol Kim, Dongho Lee, Seong Su Hong, Zhu Na, Jin Chul Shin, Su Heun Roh, Cheng-Zhu Wu, Oksik Choi, Kyeong Lee, Yue-Mao Shen, Sang-Gi Paik, Jung Joon Lee, Young-Soo Hong, Rational Biosynthetic Engineering for Optimization of Geldanamycin Analogues ChemBioChem. ,vol. 10, pp. 1243- 1251 ,(2009) , 10.1002/CBIC.200800763
Dongho Lee, Kyeong Lee, Xing Fu Cai, Nguyen Tien Dat, Shanthaveerappa K. Boovanahalli, Mijeoung Lee, Jin Chul Shin, Woncheol Kim, Jae Kap Jeong, Jong Suk Lee, Choong-Hwan Lee, Jeong-Hyung Lee, Young-Soo Hong, Jung Joon Lee, Biosynthesis of the heat-shock protein 90 inhibitor geldanamycin: new insight into the formation of the benzoquinone moiety. ChemBioChem. ,vol. 7, pp. 246- 248 ,(2006) , 10.1002/CBIC.200500441
ZHIHAO HU, YAOQUAN LIU, ZONG-QIANG TIAN, WEI MA, COURTNEY M. STARKS, RIKA REGENTIN, PETER LICARI, DAVID C. MYLES, C. RICHARD HUTCHINSON, Isolation and characterization of novel geldanamycin analogues. The Journal of Antibiotics. ,vol. 57, pp. 421- 428 ,(2004) , 10.7164/ANTIBIOTICS.57.421
M. Barginear, C. Van Poznak, N. Rosen, S. Modi, C. Hudis, D. Budman, The Heat Shock Protein 90 Chaperone Complex: An Evolving Therapeutic Target Current Cancer Drug Targets. ,vol. 8, pp. 522- 535 ,(2008) , 10.2174/156800908785699379