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FR225659

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Category Bioactive by-products
Catalog number BBF-03555
CAS
Molecular Weight 736.21
Molecular Formula C36H42ClN7O8

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

FR225659 is originally isolated from Helicomyces sp. No. 19353. It can suppress the gluconeogenesis induced by Glucagon in Primary hepatocytes of rats.

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IUPAC Name 2-[[(2S,3R)-1-[3-chloro-5-(diaminomethylideneamino)-4-hydroxy-2-[[4-hydroxy-3-(3-prop-1-en-2-ylquinolin-4-yl)benzoyl]amino]pentanoyl]-3-hydroxy-3-methylpyrrolidine-2-carbonyl]amino]-3-methylbut-2-enoic acid
Canonical SMILES CC(=C(C(=O)O)NC(=O)C1C(CCN1C(=O)C(C(C(CN=C(N)N)O)Cl)NC(=O)C2=CC(=C(C=C2)O)C3=C(C=NC4=CC=CC=C43)C(=C)C)(C)O)C
InChI InChI=1S/C36H42ClN7O8/c1-17(2)22-15-40-23-9-7-6-8-20(23)26(22)21-14-19(10-11-24(21)45)31(47)43-29(27(37)25(46)16-41-35(38)39)33(49)44-13-12-36(5,52)30(44)32(48)42-28(18(3)4)34(50)51/h6-11,14-15,25,27,29-30,45-46,52H,1,12-13,16H2,2-5H3,(H,42,48)(H,43,47)(H,50,51)(H4,38,39,41)/t25?,27?,29?,30-,36-/m1/s1
InChI Key UIKSOMFXGWTAID-DUUDCQCKSA-N
Appearance White Powder
Melting Point 225-230°C
Density 1.4±0.1 g/cm3
Solubility Soluble in DMSO
1. FR225659-binding proteins: identification as serine/threonine protein phosphatase PP1 and PP2A using high-performance affinity beads
Hidetaka Hatori, Tatsuya Zenkoh, Motoo Kobayashi, Yoshihiro Ohtsu, Nobuharu Shigematsu, Hiroyuki Setoi, Motohiro Hino, Hiroshi Handa J Antibiot (Tokyo). 2004 Jul;57(7):456-61. doi: 10.7164/antibiotics.57.456.
FR225659 was originally isolated as a novel gluconeogenesis inhibitor produced by fungal strain Helicomyces sp. No. 19353. To identify the target protein of FR225659, we synthesized high-performance affinity latex beads that immobilized FR225659 derivative FR253761 or FR259383. Using these beads, we identified FR225659 binding proteins as serine/threonine protein phosphatase type1 (PP1) and type2A (PP2A) from rat hepatocyte crude extract. FR225659 and its synthetic derivatives were strongly inhibited the enzyme activities of purified catalytic subunits of PP1 and PP2A in vitro.
2. Efficient Chemoenzymatic Synthesis of (2 S,3 R)-3-Hydroxy-3-Methylproline, a Key Fragment in Polyoxypeptin A and FR225659
Xiao Zhang, Hans Renata Tetrahedron. 2019 Jun 14;75(24):3253-3257. doi: 10.1016/j.tet.2019.04.009. Epub 2019 Apr 5.
We report an efficient synthesis of protected (2S,3R)-3-hydroxy-3-methylproline that proceeds in three steps with complete stereoselectivity. This route represents a significant improvement over previous approaches to this noncanonical amino acid. Key to this success is the development of a one-pot chemoenzymatic procedure for the preparation of (2S,3S)-3- methylproline from L-isoleucine. This work lays the foundation for future chemoenzymatic syntheses of polyoxypeptin A and FR225659.
3. Design and synthesis of a solid-supported FR225659 derivative for its receptor screening
Tatsuya Zenkoh, Hidetaka Hatori, Hiroshi Tanaka, Makoto Hasegawa, Mamoru Hatakeyama, Yasuaki Kabe, Hiroyuki Setoi, Haruma Kawaguchi, Hiroshi Handa, Takashi Takahashi Org Lett. 2004 Jul 8;6(14):2477-80. doi: 10.1021/ol049100q.
[structure: see text] We describe the design and synthesis of latex particles attached to an FR225659 derivative to identify its receptor proteins. Two key building blocks were prepared by two-step degradation of FR225659 under basic conditions. The designed ligand showed an acceptable level of biological activity to make it of potential value for use in affinity-supported receptor identification. Affinity purification of FR225659-binding proteins using the latex nanoparticles provided three candidate receptor peptides for the biological activity.

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