Saframycin G
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| Category | Antibiotics |
| Catalog number | BBF-02846 |
| CAS | 92569-02-3 |
| Molecular Weight | 578.57 |
| Molecular Formula | C29H30N4O9 |
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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 has the effect of inhibiting mouse lymphocyte L-1210 with ID50 of 0.03 μmol/L.
Specification
| Synonyms | 14-Hydroxysaframycin A; Propanamide, N-[[(5S,6R,7R,9R,14aS,15R)-7-cyano-1,5,6,7,9,10,13,14,14a,15-decahydro-5-hydroxy-2,11-dimethoxy-3,12,16-trimethyl-1,4,10,13-tetraoxo-6,15-imino-4H-isoquino[3,2-b][3]benzazocin-9-yl]methyl]-2-oxo-; Propanamide, N-[(7-cyano-1,5,6,7,9,10,13,14,14a,15-decahydro-5-hydroxy-2,11-dimethoxy-3,12,16-trimethyl-1,4,10,13-tetraoxo-6,15-imino-4H-isoquino[3,2-b][3]benzazocin-9-yl)methyl]-2-oxo-, [5S-(5a,6a,7a,9b,14aa,15a)]-; (-)-Saframycin G; Propanamide, N-((7-cyano-1,5,6,7,9,10,13,14,14a,15-decahydro-5-hydroxy-2,11-dimethoxy-3,12,16-trimethyl-1-4-10,13-tetraoxo-6,15-imino-4H-isoquino(3,2-b)(3)benzazocin-9-yl)methyl)-2-oxo-, (5S-(5alpha,6alpha,7alpha,9beta,14aalpha,15alpha))- |
| IUPAC Name | N-[[(1R,2S,10R,13R,14S)-12-cyano-14-hydroxy-7,18-dimethoxy-6,17,21-trimethyl-5,8,16,19-tetraoxo-11,21-diazapentacyclo[11.7.1.02,11.04,9.015,20]henicosa-4(9),6,15(20),17-tetraen-10-yl]methyl]-2-oxopropanamide |
| Canonical SMILES | CC1=C(C(=O)C2=C(C1=O)CC3C4C5=C(C(C(N4C)C(N3C2CNC(=O)C(=O)C)C#N)O)C(=O)C(=C(C5=O)OC)C)OC |
| InChI | InChI=1S/C29H30N4O9/c1-10-22(35)13-7-14-20-18-19(23(36)11(2)28(42-6)26(18)39)24(37)21(32(20)4)15(8-30)33(14)16(9-31-29(40)12(3)34)17(13)25(38)27(10)41-5/h14-16,20-21,24,37H,7,9H2,1-6H3,(H,31,40)/t14-,15?,16-,20-,21+,24-/m0/s1 |
| InChI Key | YQQUMADRNAOVHP-SEBJRLBMSA-N |
Properties
| Appearance | Yellow Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Neoplastics (Tumor) |
| Melting Point | 134-136°C (dec.) |
| Density | 1.48 g/cm3 |
| Solubility | Soluble in Methanol, Chloroform |
Reference Reading
1. Structural studies on minor components of saframycin group antibiotics saframycins F, G and H
Y Mikami, K Takahashi, K Yazawa, C Hour-Young, T Arai, N Saito, A Kubo J Antibiot (Tokyo). 1988 Jun;41(6):734-40. doi: 10.7164/antibiotics.41.734.
Three minor components of saframycin group antibiotics, saframycins F, G and H were isolated and their structures were determined by comparison with the spectral data of UV, IR, and 1H and 13C NMR of already reported saframycins A and D. Saframycins F, G and H were 21-cyanosaframycin D, 14-hydroxysaframycin A and 25-dihydro-25-beta-ketopropyl-saframycin A, respectively.
2. 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.
3. Synthesis of saframycins. X. Transformation of (-)-saframycin A to (-)-saframycin Mx type compound with the structure proposed for saframycin E
N Saito, S Harada, M Nishida, I Inouye, A Kubo Chem Pharm Bull (Tokyo). 1995 May;43(5):777-82. doi: 10.1248/cpb.43.777.
Treatment of (-)-saframycin A (1a) with selenium oxide in acetic acid afforded (-)-saframycin G (1g), and a catalytic reduction and regioselective oxidation sequence afforded the saframycin Mx type compound (3). We applied this methodology to the transformation of (+/-)-5-hydroxysaframycin B (11) to the hydroquinone (1e). Acetylation of 1e with acetic anhydride in pyridine gave the triacetate (13), which is identical with the triacetyl derivative of natural saframycin E.
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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 ╳
