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FL-120B

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Category Antibiotics
Catalog number BBF-03544
CAS 156429-11-7
Molecular Weight 422.39
Molecular Formula C22H18N2O7

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Fermentation Lab

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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

FL-120B is produced by the strain of Streptomyces chattanoogensis subsp. taitungessis. It has anti-Gram-positive aerobes and anaerobe activity.

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Synonyms 9-Diazonio-2,7-dihydroxy-10a-methyl-10-[(2-methylpropanoyl)oxy]-8-oxo-2,8,10,10a-tetrahydro-1aH-benzo[6,7]fluoreno[2,3-b]oxiren-3-olate
IUPAC Name [(3R,4R,6R,7S)-9-diazo-3,13-dihydroxy-6-methyl-11,18-dioxo-5-oxapentacyclo[8.8.0.02,8.04,6.012,17]octadeca-1(10),2(8),12(17),13,15-pentaen-7-yl] 2-methylpropanoate
Canonical SMILES CC(C)C(=O)OC1C2=C(C(C3C1(O3)C)O)C4=C(C2=[N+]=[N-])C(=O)C5=C(C4=O)C=CC=C5O
InChI InChI=1S/C22H18N2O7/c1-7(2)21(29)30-19-14-12(18(28)20-22(19,3)31-20)11-13(15(14)24-23)17(27)10-8(16(11)26)5-4-6-9(10)25/h4-7,18-20,25,28H,1-3H3/t18-,19+,20-,22-/m1/s1
InChI Key RPARKPVSEAVPID-XAPVIXHLSA-N
Appearance Orange Acicular Crystals
Antibiotic Activity Spectrum Gram-positive bacteria
Melting Point 185-190°C
1. FL-120A-D', new products related to kinamycin from Streptomyces chattanoogensis subsp. taitungensis subsp. nov. II. Isolation and structure determination
J J Young, S N Ho, W M Ju, L R Chang J Antibiot (Tokyo). 1994 Jun;47(6):681-7. doi: 10.7164/antibiotics.47.681.
Six new kinamycin antibiotics have been isolated from the culture filtrate of Streptomyces chattanoogensis. The structures of six related components were determined employing 1D and 2D NMR spectroscopy and mass spectrometry. These structures represent the first reported epoxide kinamycin (2, 3) and propionyl derivative of kinamycin (5), and new isobutyryl derivatives of kinamycin (1, 4, 6).
2. Asymmetric total synthesis of the epoxykinamycin FL-120 B'
Stephen S Scully, John A Porco Jr Angew Chem Int Ed Engl. 2011 Oct 4;50(41):9722-6. doi: 10.1002/anie.201104504. Epub 2011 Aug 30.
Turn up the heat: An asymmetric total synthesis of the epoxykinamycin FL-120B' is reported. The synthesis establishes a route to epoxide-containing diazobenzofluorenes which could potentially serve as monomers to the dimeric lomaiviticins. Key steps include Sharpless asymmetric epoxidation, Stille coupling, and intramolecular Friedel-Crafts acylation of atropisomeric carboxylic acids at elevated temperatures to construct the FL-120B' core structure.
3. Studies toward the synthesis of the epoxykinamycin FL-120B': discovery of a decarbonylative photocyclization
Stephen S Scully, John A Porco Jr Org Lett. 2012 May 18;14(10):2646-9. doi: 10.1021/ol3010563. Epub 2012 May 9.
Photo-Friedel-Crafts acylation of a naphthoquinone was attempted in an effort to access a diazobenzofluorenone en route to the epoxykinamycin natural product FL-120B'. Photoirradiation of the naphthoquinone substrate which resulted in the unexpected formation of a tetracyclic naphthofuran via a decarbonylative photocyclization process is described.
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