142383-53-7Relevant academic research and scientific papers
Substrate Recognition by a Dual-Function P450 Monooxygenase GfsF Involved in FD-891 Biosynthesis
Miyanaga, Akimasa,Takayanagi, Ryuichi,Furuya, Takashi,Kawamata, Ayano,Itagaki, Tomohiro,Iwabuchi, Yoshiharu,Kanoh, Naoki,Kudo, Fumitaka,Eguchi, Tadashi
, p. 2179 - 2187 (2017/10/07)
GfsF is a multifunctional P450 monooxygenase that catalyzes epoxidation and subsequent hydroxylation in the biosynthesis of macrolide polyketide FD-891. Here, we describe the biochemical and structural analysis of GfsF. To obtain the structural basis of a
Synthesis and structure-activity relationship study of FD-891: Importance of the side chain and C8-C9 epoxide for cytotoxic activity against cancer cells
Itagaki, Tomohiro,Kawamata, Ayano,Takeuchi, Miho,Hamada, Keisuke,Iwabuchi, Yoshiharu,Eguchi, Tadashi,Kudo, Fumitaka,Usui, Takeo,Kanoh, Naoki
, p. 287 - 293 (2016/05/09)
Unified synthesis of FD-891 analogs and their structure-activity relationship are described. By using stereoselective allylation/crotylation and Evans aldol chemistry, six side-chain fragments having different length and terminus were synthesized. These f
Stereoselective total synthesis of FD-891
Yadav,Das, Sukant Kishore,Sabitha
, p. 11109 - 11118 (2013/02/23)
FD-891, a structurally unique 16-membered macrolide having anticancer activity, was synthesized according to a strategy employing asymmetric allylation, Prins cyclization, cross-metathesis reaction, Yamaguchi lactonization, and Julia-Kocienski olefination
Cloning and characterization of the biosynthetic gene cluster of 16-membered macrolide antibiotic FD-891: Involvement of a dual functional cytochrome P450 monooxygenase catalyzing epoxidation and hydroxylation
Kudo, Fumitaka,Motegi, Atsushi,Mizoue, Kazutoshi,Eguchi, Tadashi
body text, p. 1574 - 1582 (2011/04/22)
FD-891 is a 16-membered cytotoxic antibiotic macrolide that is especially active against human leukemia such as HL-60 and Jurkat cells. We identified the FD-891 biosynthetic (gfs) gene cluster from the producer Streptomyces graminofaciens A-8890 by using
The total synthesis and biological properties of the cytotoxic macrolide FD-891 and its non-natural (Z)-C12 isomer
Garcia-Fortanet, Jorge,Murga, Juan,Carda, Miguel,Marco, J. Alberto,Matesanz, Ruth,Diaz, J. Fernando,Barasoain, Isabel
, p. 5060 - 5074 (2008/02/11)
A total, stereoselective synthesis of the naturally occurring, cytotoxic macrolide FD-891 and of its non-natural (Z)-C12 isomer is described. Three fragments of the main carbon chain were stereoselectively prepared by using asymmetric aldol and allylation reactions as the key steps. The molecule was then assembled by using two Julia-Kocienski olefinations to connect the three fragments and a Yamaguchi reaction to close the macrolactone ring. Some specific biological properties (cytotoxicity, binding to tubulin) have been determined for both macrolides. The E configuration of the C12-C13 olefinic bond seems to be an important feature in determining the cytotoxicity but the precise biological mechanism of the latter still remains to be cleared.
Enantioselective total synthesis of FD-891
Crimmins, Michael T.,Caussanel, Franck
, p. 3128 - 3129 (2007/10/03)
The enantioselective synthesis of FD-891 has been achieved with a longest linear sequence of 21 steps. The synthetic strategy involves the use of aldol additions of a chlorotitanium enolate of N-acylthiazolidinethiones as the key reaction to establish 6 o
