R1128 D
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| Category | Bioactive by-products |
| Catalog number | BBF-03360 |
| CAS | 135161-99-8 |
| Molecular Weight | 326.3 |
| Molecular Formula | C19H18O5 |
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Description
R1128 D is a non-steroidal estrogen-receptor antagonist produced by Streptomyces sp. No. 1128. The IC50 value of R1128 D for partially purified rat uterine cytosol receptor was 2.7 x 10(-7) M.
Specification
| Synonyms | R1128D; R-1128D |
| IUPAC Name | 1,3,6-trihydroxy-8-pentylanthracene-9,10-dione |
| Canonical SMILES | CCCCCC1=C2C(=CC(=C1)O)C(=O)C3=C(C2=O)C(=CC(=C3)O)O |
| InChI | InChI=1S/C19H18O5/c1-2-3-4-5-10-6-11(20)7-13-16(10)19(24)17-14(18(13)23)8-12(21)9-15(17)22/h6-9,20-22H,2-5H2,1H3 |
| InChI Key | BAAGPGLSSCBBBB-UHFFFAOYSA-N |
Properties
| Appearance | Brown Powder |
| Melting Point | 237-242°C |
Reference Reading
1. Biosynthesis of aromatic polyketides in bacteria
Abhirup Das, Chaitan Khosla Acc Chem Res. 2009 May 19;42(5):631-9. doi: 10.1021/ar8002249.
Natural products, produced chiefly by microorganisms and plants, can be large and structurally complex molecules. These molecules are manufactured by cellular assembly lines, in which enzymes construct the molecules in a stepwise fashion. The means by which enzymes interact and work together in a modular fashion to create diverse structural features has been an active area of research; the work has provided insight into the fine details of biosynthesis. A number of polycyclic aromatic natural products--including several noteworthy anticancer, antibacterial, antifungal, antiviral, antiparasitic, and other medicinally significant substances--are synthesized by polyketide synthases (PKSs) in soil-borne bacteria called actinomycetes. Concerted biosynthetic, enzymological, and structural biological investigations into these modular enzyme systems have yielded interesting mechanistic insights. A core module called the minimal PKS is responsible for synthesizing a highly reactive, protein-bound poly-beta-ketothioester chain. In the absence of other enzymes, the minimal PKS also catalyzes chain initiation and release, yielding an assortment of polycyclic aromatic compounds. In the presence of an initiation PKS module, polyketide backbones bearing additional alkyl, alkenyl, or aryl primer units are synthesized, whereas a range of auxiliary PKS enzymes and tailoring enzymes convert the product of the minimal PKS into the final natural product. In this Account, we summarize the knowledge that has been gained regarding this family of PKSs through recent investigations into the biosynthetic pathways of two natural products, actinorhodin and R1128 (A-D). We also discuss the practical relevance of these fundamental insights for the engineered biosynthesis of new polycyclic aromatic compounds. With a deeper understanding of the biosynthetic process in hand, we can assert control at various stages of molecular construction and thus introduce unnatural functional groups in the process. The metabolic engineer affords a number of new avenues for creating novel molecular structures that will likely have properties akin to their fully natural cousins.
2. R1128 substances, novel non-steroidal estrogen-receptor antagonists produced by a Streptomyces. II. Physico-chemical properties and structure determination
Y Hori, S Takase, N Shigematsu, T Goto, M Okuhara, M Kohsaka J Antibiot (Tokyo). 1993 Jul;46(7):1063-8. doi: 10.7164/antibiotics.46.1063.
R1128 A, B, C and D, new non-steroidal estrogen-receptor antagonists, were isolated from the cultured broth of Streptomyces sp. No. 1128. Their structures were elucidated to be 1,3,6-trihydroxy-8-alkylanthraquinones on the basis of their physico-chemical properties and spectroscopic data.
3. De novo biosynthesis of carminic acid in Saccharomyces cerevisiae
Qian Zhang, Xinglong Wang, Weizhu Zeng, Sha Xu, Dong Li, Shiqin Yu, Jingwen Zhou Metab Eng. 2023 Jan 10;76:50-62. doi: 10.1016/j.ymben.2023.01.005. Online ahead of print.
Carminic acid is a natural red dye extracted from the insect Dactylopius coccus. Due to its ideal dying effect and high safety, it is widely used in food and cosmetics industries. Previous study showed that introduction of polyketide synthase (OKS) from Aloe arborescens, cyclase (ZhuI) and aromatase (ZhuJ) from Streptomyces sp. R1128, and C-glucosyltransferase (UGT2) from D. coccus into Aspergillus nidulans could achieve trace amounts of de novo production. These four genes were introduced into Saccharomyces cerevisiae, but carminic acid was not detected. Analysis of the genome of A. nidulans revealed that 4'-phosphopantetheinyl transferase (NpgA) and monooxygenase (AptC) are essential for de novo biosynthesis of carminic acid in S. cerevisiae. Additionally, endogenous hydroxylase (Cat5) from S. cerevisiae was found to be responsible for hydroxylation of flavokermesic acid to kermesic acid. Therefore, all enzymes and their functions in the biosynthesis of carminic acid were explored and reconstructed in S. cerevisiae. Through systematic pathway engineering, including regulating enzyme expression, enhancing precursor supply, and modifying the β-oxidation pathway, the carminic acid titer in a 5 L bioreactor reached 7580.9 μg/L, the highest yet reported for a microorganism. Heterologous reconstruction of the carminic acid biosynthetic pathway in S. cerevisiae has great potential for de novo biosynthesis of anthraquinone dye.
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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 ╳
