Safracin B

Safracin B

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Safracin B
Category Antineoplastic
Catalog number BBF-02219
CAS 87578-99-2
Molecular Weight 540.61
Molecular Formula C28H36N4O7
Purity ≥85% (HPLC)

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Safracin B is a new antibiotic from the family of Safracin produced by Pseudomonas fluorescens A2-2. Safracin B exhibits broad spectrum antimicrobial and strong antitumor activities.


Related CAS 82029-27-4
Synonyms Antibiotic EM 5519; Antibiotic Y 16482α
IUPAC Name (2S)-2-amino-N-[[(1S,2S,10R,12S,13R)-12,19-dihydroxy-7,18-dimethoxy-6,17,21-trimethyl-5,8-dioxo-11,21-diazapentacyclo[,11.04,9.015,20]henicosa-4(9),6,15(20),16,18-pentaen-10-yl]methyl]propanamide
Canonical SMILES CC1=CC2=C(C3C4CC5=C(C(N4C(C(C2)N3C)O)CNC(=O)C(C)N)C(=O)C(=C(C5=O)C)OC)C(=C1OC)O
InChI InChI=1S/C28H36N4O7/c1-11-7-14-8-17-28(37)32-16(21(31(17)4)19(14)23(34)25(11)38-5)9-15-20(18(32)10-30-27(36)13(3)29)24(35)26(39-6)12(2)22(15)33/h7,13,16-18,21,28,34,37H,8-10,29H2,1-6H3,(H,30,36)/t13-,16-,17+,18-,21+,28-/m0/s1


Appearance Yellow to Brown powder
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria; neoplastics (Tumor)
Boiling Point 755.1°C at 760 mmHg
Melting Point >260°C
Density 1.41 g/cm3

Reference Reading

1. Biosynthesis of Tetrahydroisoquinoline Antibiotics
Li-Qiang Song, Man-Cheng Tang, Gong-Li Tang, Yue Zhang Curr Top Med Chem . 2016;16(15):1717-26. doi: 10.2174/1568026616666151012112329.
The tetrahydroisoquinoline (THIQ) alkaloids are naturally occurring antibiotics isolated from a variety of microorganisms and marine invertebrates. This family of natural products exhibit broad spectrum antimicrobial and strong antitumor activities, and the potency of clinical application has been validated by the marketing of ecteinascidin 743 (ET-743) as anticancer drug. In the past 20 years, the biosynthetic gene cluster of six THIQ antibiotics has been characterized including saframycin Mx1 from Myxococcus xanthus, safracin-B from Pseudomonas fluorescens, saframycin A, naphthyridinomycin, and quinocarcin from Streptomyces, as well as ET-743 from Ecteinascidia turbinata. This review gives a brief summary of the current status in understanding the molecular logic for the biosynthesis of these natural products, which provides new insights on the biosynthetic machinery involved in the nonribosomal peptide synthetase system. The proposal of the THIQ biosynthetic pathway not only shows nature's route to generate such complex molecules, but also set the stage to develop a different process for production of ET-743 by synthetic biology.
2. Characterization of the saframycin A gene cluster from Streptomyces lavendulae NRRL 11002 revealing a nonribosomal peptide synthetase system for assembling the unusual tetrapeptidyl skeleton in an iterative manner
Gong-Li Tang, Wei Ding, Jie Song, Wei Deng, Qun-Fei Zhao, Chao Peng, Wei-Wen Song, Lei Li, Wen Liu J Bacteriol . 2008 Jan;190(1):251-63. doi: 10.1128/JB.00826-07.
Saframycin A (SFM-A), produced by Streptomyces lavendulae NRRL 11002, belongs to the tetrahydroisoquinoline family of antibiotics, and its core is structurally similar to the core of ecteinascidin 743, which is a highly potent antitumor drug isolated from a marine tunicate. In this study, the biosynthetic gene cluster for SFM-A was cloned and localized to a 62-kb contiguous DNA region. Sequence analysis revealed 30 genes that constitute the SFM-A gene cluster, encoding an unusual nonribosomal peptide synthetase (NRPS) system and tailoring enzymes and regulatory and resistance proteins. The results of substrate prediction and in vitro characterization of the adenylation specificities of this NRPS system support the hypothesis that the last module acts in an iterative manner to form a tetrapeptidyl intermediate and that the colinearity rule does not apply. Although this mechanism is different from those proposed for the SFM-A analogs SFM-Mx1 and safracin B (SAC-B), based on the high similarity of these systems, it is likely they share a common mechanism of biosynthesis as we describe here. Construction of the biosynthetic pathway of SFM-Y3, an aminated SFM-A, was achieved in the SAC-B producer (Pseudomonas fluorescens). These findings not only shed new insight on tetrahydroisoquinoline biosynthesis but also demonstrate the feasibility of engineering microorganisms to generate structurally more complex and biologically more active analogs by combinatorial biosynthesis.
3. Safracins, new antitumor antibiotics. I. Producing organism, fermentation and isolation
H Idemoto, T Asao, F Hirayama, K Iwao, T Munakata, K Yamamoto, Y Ikeda J Antibiot (Tokyo) . 1983 Oct;36(10):1279-83. doi: 10.7164/antibiotics.36.1279.
Safracins, new antibiotics with a novel skeleton, were discovered in a culture broth of Pseudomonas sp. The producing organism has been identified as Pseudomonas fluorescens. Safracins A and B were isolated by ethyl acetate extraction and chromatography on silica gel.

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