Saframycin D
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| Category | Antibiotics |
| Catalog number | BBF-02843 |
| CAS | 66082-30-2 |
| Molecular Weight | 553.56 |
| Molecular Formula | C28H31N3O9 |
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Description
It is produced by the strain of Str. lavendulae No 314. It has the effect of anti-Gram-positive bacteria, and Saframycin A has the strongest antibacterial activity. It also has weak activity against mycobacteria.
Specification
| Synonyms | N-[[(6R)-6,7,9,10,13,14,14aα,15-Octahydro-1,4-dihydroxy-2,11-dimethoxy-3,12,16-trimethyl-5,10,13-trioxo-6α,15α-epimino-5H-isoquino[3,2-b][3]benzazocin-9β-yl]methyl]-2-oxopropionamide; Propanamide, N-[[(6R,9R,14aS,15R)-6,7,9,10,13,14,14a,15-octahydro-1,4-dihydroxy-2,11-dimethoxy-3,12,16-trimethyl-5,10,13-trioxo-6,15-imino-5H-isoquino[3,2-b][3]benzazocin-9-yl]methyl]-2-oxo-; Propanamide, N-((6,7,9,10,13,14,14a,15-octahydro-1,4-dihydroxy-2,11-dimethoxy-3,12,16-trimethyl-5,10,13-trioxo-6,15-imino-5H-isoquino(3,2-b)(3)benzazocin-9-yl)methyl)-2-oxo-, (6R-(6-alpha,9-beta,14a-alpha,15-alpha))- |
| IUPAC Name | N-[[(1R,2S,10R,13R)-16,19-dihydroxy-7,18-dimethoxy-6,17,21-trimethyl-5,8,14-trioxo-11,21-diazapentacyclo[11.7.1.02,11.04,9.015,20]henicosa-4(9),6,15(20),16,18-pentaen-10-yl]methyl]-2-oxopropanamide |
| Canonical SMILES | CC1=C(C2=C(C3C4CC5=C(C(N4CC(C2=O)N3C)CNC(=O)C(=O)C)C(=O)C(=C(C5=O)C)OC)C(=C1OC)O)O |
| InChI | InChI=1S/C28H31N3O9/c1-10-21(33)13-7-14-20-18-19(22(34)11(2)27(40-6)25(18)37)23(35)16(30(20)4)9-31(14)15(8-29-28(38)12(3)32)17(13)24(36)26(10)39-5/h14-16,20,34,37H,7-9H2,1-6H3,(H,29,38)/t14-,15-,16+,20-/m0/s1 |
| InChI Key | JRGSNFZUTBSLSG-MFCZKXCZSA-N |
Properties
| Appearance | Yellow Acicular Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Mycobacteria |
| Melting Point | 150-154°C |
| Density | 1.49 g/cm3 |
| Solubility | Soluble in Methanol, Chloroform, Ethyl Acetate, Acetone, Ether, Benzene |
Reference Reading
1. Biosynthesis of 3-hydroxy-5-methyl-o-methyltyrosine in the saframycin/ safracin biosynthetic pathway
Cheng-Yu Fu, Man-Cheng Tang, Chao Peng, Lei Li, Yan-Ling He, Wen Liu, Gong-Li Tang J Microbiol Biotechnol. 2009 May;19(5):439-46. doi: 10.4014/jmb.0808.484.
The biosynthesis study of antibiotics saframycin (SFM) in Streptomyces lavendulae and safracin (SAC) in Pseudomonas fluorescens demonstrated that 3-hydroxy-5-methyl-Omethyltyrosine (3h5mOmTyr), a nonproteinogenic amino acid, is the precursor of the tetrahydroisoquinoline molecular core. In the biosynthetic gene cluster of SAC/SFM, sacD/ sfmD encodes a protein with high homology to each other but no sequence similarity to other known enzymes; sacF/ sfmM2 and sacG/sfmM3 encode methyltransferases for Cmethylation and O-methylation; and sacE/sfmF encodes a small protein with significant sequence similarity to the MbtH-like proteins, which are frequently found in the biosynthetic pathways of nonribosomal peptide antibiotics and siderophores. To address their function, the biosynthetic cassette of 3h5mOmTyr was heterologously expressed in S. coelicolor and P. putida, and an in-frame deletion and complementation in trans were carried out. The results revealed that (i) SfmD catalyzes the hydroxylation of aromatic rings;(ii) sacD/sacF/sacG in the SAC gene cluster and sfmD/sfmM2/sfmM3 in the SFM cluster are sufficient for the biosynthesis of 3h5mOmTyr; and (iii) the mbtH-like gene is not required for the biosynthesis of the 3h5mOmTyr precursor.
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Bio Calculators
* 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 ╳
