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FR 900482

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Category Antibiotics
Catalog number BBF-03565
CAS 102363-08-6
Molecular Weight 321.28
Molecular Formula C14H15N3O6

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Capabilities & Facilities

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

FR 900482 is produced by the strain of Streptomyces sandaensis No. 6897. It is highly sensitive to Bacillus stearothermophilus var. calidolactis C 953 and has anti-P388, B16, EL4, FM3A, L1210, BHK-21 and other cell activities.

  • Specification
  • Properties
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Synonyms Antibiotic FR 900482; BRN 4886722; (5-Formyl-7,9-dihydroxy-1,1a,2,8,9,9a-hexahydro-3,9-epoxyazireno[2,3-c][1]benzazocin-8-yl)methyl hydrogen carbonimidate
IUPAC Name [(8R,9R,10R,12R)-4-formyl-6,9-dihydroxy-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2(7),3,5-trien-8-yl]methyl carbamate
Canonical SMILES C1C2C(N2)C3(C(C4=C(N1O3)C=C(C=C4O)C=O)COC(=O)N)O
InChI InChI=1S/C14H15N3O6/c15-13(20)22-5-7-11-9(1-6(4-18)2-10(11)19)17-3-8-12(16-8)14(7,21)23-17/h1-2,4,7-8,12,16,19,21H,3,5H2,(H2,15,20)/t7-,8+,12+,14+/m0/s1
InChI Key XVPSPMLUMQEEIU-PWLJWKHCSA-N
Appearance White Powder
Antibiotic Activity Spectrum Gram-positive bacteria; neoplastics (Tumor)
Boiling Point 572.3±60.0°C at 760 mmHg
Melting Point 175°C
Density 1.7±0.1 g/cm3
1. 6-Bromomethyl-4H-1,3-dioxin: a versatile bromomethyl vinyl ketone equivalent for heterocycle and carbocycle construction
Thomas J Greshock, Raymond L Funk J Am Chem Soc. 2002 Feb 6;124(5):754-5. doi: 10.1021/ja0123554.
6-Bromomethyl-4H-1,3-dioxin has been prepared in three steps from allyl iodide. A variety of enolates were then alkylated with this bromide. The resulting 6-alkyl-4H-1,3-dioxins were either subjected to further multistep transformations and/or heated to effect facile retrocycloaddition reactions. The resulting enones smoothly participated in novel endo-conjugate addition reactions with both carbon and nitrogen nucleophiles. For example, several bicyclo[4.3.1]decan-3,10-diones, the carbon framework of the CP compounds, were constructed using this novel annulation strategy. In another natural product study, a benzazocine related to the heterocyclic framework of the ring-opened tautomeric form of FR-900482 was also prepared using this methodology. Finally, a piperidin-4-one obtained from a 6-endo conjugate addition was converted to the naturally occurring (2S,4R)-4-hydroxypipecolic acid. Collectively, these examples document the synthetic equivalency of dioxin 1 with bromomethyl vinyl ketone and, moreover, delineate a strategy for accomplishing the sequential reactions with nucleophiles at the alpha' followed by the beta electrophilic sites.
2. Total synthesis of natural product DNA cross-linking agents
R S Coleman Curr Opin Drug Discov Devel. 2001 Jul;4(4):435-49.
A variety of naturally occurring compounds interact with duplex DNA by the formation of covalent cross-links. This review describes recent progress on the total synthesis of four natural product families, including the mitomycins, the structurally and functionally related agent FR-900482, the bis-pyrrole isochrysohermidine and the azinomycins.
3. Intramolecular 1,3-dipolar cycloaddition strategy for enantioselective synthesis of FR-900482 analogues
M Kambe, E Arai, M Suzuki, H Tokuyama, T Fukuyama Org Lett. 2001 Aug 9;3(16):2575-8. doi: 10.1021/ol016243t.
[reaction: see text] Enantioselective synthesis of FR-900482 analogues is described. The key reaction of the synthesis is intramolecular 1,3-dipolar cycloaddition of a highly functionalized nitrile oxide with complete stereo- and regioselectivities to construct the eight-membered benzazocine ring.

Bio Calculators

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* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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