Author: Miyanaga, Akimasa ; Furuya, Takashi ; Kudo, Fumitaka ; Kawamura, Koichi ; Komatsubara, Akiko ; Eguchi, Tadashi ; Yamanishi, Hiroto ; Motegi, Atsushi ; Numakura, Mario

AbstractTo isolate a key polyketide biosynthetic intermediate for the 16‐membered macrolide FD‐891 (1), we inactivated two biosynthetic genes coding for post‐polyketide synthase (PKS) modification enzymes: a methyltransferase (GfsG) and a cytochrome P450 (GfsF). Consequently, FD‐892 (2), which lacks the epoxide moiety at C8–C9, the hydroxy group at C10, and the O‐methyl group at O‐25 of FD‐891, was isolated from the gfsF/gfsG double‐knockout mutant. In addition, 25‐O‐methyl‐FD‐892 (3) and 25‐O‐demethyl‐FD‐891 (4) were isolated from the gfsF and gfsG mutants, respectively. We also confirmed that GfsG efficiently catalyzes the methylation of 2 and 4 in vitro. Further, GfsF catalyzed the epoxidation of the double bond at C8‐C9 of 2 and 3 and subsequent hydroxylation at C10, to afford 4 and 1, respectively. These results suggest that a parallel post‐PKS modification mechanism is involved in FD‐891 biosynthesis.

03 Oct 2014·Organic LettersQ1 · CHEMISTRY

A Concise and Unified Strategy for Synthesis of the C1–C18 Macrolactone Fragments of FD-891, FD-892 and Their Analogues: Formal Total Synthesis of FD-891

Q1 · CHEMISTRY

Article

Author: Kwon, Eunsang ; Miyazaki, Yuta ; Kanoh, Naoki ; Itagaki, Tomohiro ; Yahata, Kenzo ; Iwabuchi, Yoshiharu ; Kawamata, Ayano

A concise and unified strategy for the synthesis of C1-C18 macrolactone fragments of FD-891 and FD-892 as well as their analogues is reported. The strategy includes a stereoselective vinylogous Mukaiyama aldol reaction (VMAR) using chiral silyl ketene N,O-acetal to construct C6-C7 stereocenters, an E-selective ring closing metathesis to construct a C12-C13 olefin, and stereodivergent construction of a C8-C9 epoxide.

03 Sep 2010·ChemBioChem

Corrigendum: 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

Author: Motegi, Atsushi ; Mizoue, Kazutoshi ; Kudo, Fumitaka ; Eguchi, Tadashi

On page 1576, Table 1 is incorrect; the correct version of the table is given.On page 1578, the caption to Figure 5 is incorrect; the correct version of the caption is given.

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Indication	Highest Phase	Country/Location	Organization	Date
Neoplasms	Preclinical	Japan	Taisho Pharmaceutical Co., Ltd.	-

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