Quinocarcin
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| Category | Antibiotics |
| Catalog number | BBF-02801 |
| CAS | 84573-33-1 |
| Molecular Weight | 330.38 |
| Molecular Formula | C18H22N2O4 |
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Description
Quinocarcin is originally isolated from Streptomyces melanovinaceus. It has anti-gram-positive bacteria and Klebsiella pneumoniae activity, and also has anti-mouse leukemia P388 effect.
Specification
| Synonyms | Antibiotic DC 52; DC 52; 11-Methoxy-12-methyl-2a,3,4,5,6,6a,7,11b-octahydro-1H-3,6-epimino-2-oxa-11c-azanaphtho[1,2,3-cd]azulene-5-carboxylic acid; (2aR,3S,5R,6R,6aS,11bR)-2a,3,4,5,6,6a,7,11b-Octahydro-11-methoxy-12-methyl-3,6-imino-1H-2-oxa-11c-azanaphth[1,2,3-cd]azulene-5-carboxylic Acid |
| IUPAC Name | (1S,2R,3R,5S,6R,9R)-11-methoxy-18-methyl-7-oxa-17,18-diazapentacyclo[7.7.1.12,5.06,17.010,15]octadeca-10(15),11,13-triene-3-carboxylic acid |
| Canonical SMILES | CN1C2CC(C1C3CC4=C(C5N3C2OC5)C(=CC=C4)OC)C(=O)O |
| InChI | InChI=1S/C18H22N2O4/c1-19-12-7-10(18(21)22)16(19)11-6-9-4-3-5-14(23-2)15(9)13-8-24-17(12)20(11)13/h3-5,10-13,16-17H,6-8H2,1-2H3,(H,21,22)/t10-,11+,12+,13+,16-,17-/m1/s1 |
| InChI Key | VOUMVHRRAVBACH-RXCQEBQVSA-N |
Properties
| Appearance | Colorless Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; neoplastics (Tumor) |
| Boiling Point | 521.3±50.0°C at 760 mmHg |
| Melting Point | 170°C |
| Density | 1.4±0.1 g/cm3 |
Reference Reading
1. Asymmetric Total Synthesis of (+)-Quinocarcinamide
Lei Li, Li Shi, Kun Wei, Yu-Rong Yang Org Lett. 2021 Oct 15;23(20):7972-7975. doi: 10.1021/acs.orglett.1c02970. Epub 2021 Sep 29.
The first asymmetric total synthesis of (+)-quinocarcinamide (3), an enantiomer of the natural oxidation product from antitumor antibiotic (-)-quinocarcin (1), is described. Key steps include an iridium-catalyzed asymmetric allylic amidation of racemic alcohol 9, olefin cross-metathesis followed by a SN2' to forge tetrahydroisoquinoline, and stereocontrolled 1,3-dipolar cycloaddition between a facilely generated azomethine ylide and tert-butyl acrylate to construct the diazabicyclo[3.2.1]octane ring.
2. Biosynthesis of Tetrahydroisoquinoline Antibiotics
Gong-Li Tang, Man-Cheng Tang, Li-Qiang Song, 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.
3. Scalable Formal Synthesis of (-)-Quinocarcin
Sheng-Long Fang, Meng-Xue Jiang, Shuo Zhang, Yong-Jie Wu, Bing-Feng Shi Org Lett. 2019 Jun 21;21(12):4609-4613. doi: 10.1021/acs.orglett.9b01511. Epub 2019 Jun 10.
A scalable and unified strategy is described for the synthesis of (-)-quinocarcin, an important tetrahydroisoquinoline antitumor alkaloid. The strategy allows the practical formal synthesis of (-)-quinocarcin in 13 steps and 4.8% overall yield using N-phthaloyl-l-alanine as a chiral pool. It features the gram-scale and stereoselective synthesis of the tetrahydroisoquinoline moiety (AB ring) via Pd-catalyzed C(sp3)-H arylation and Pictet-Spengler condensation and a Cu(I)-catalyzed exo-selective [C + NC + CC] coupling reaction to generate the chiral pyrrolidine motif (D ring).
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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 ╳
