Lymphostin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02285 |
| CAS | 191474-39-2 |
| Molecular Weight | 310.31 |
| Molecular Formula | C16H14N4O3 |
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Description
It is produced by the strain of Str. sp. K Y 11783. It's an immunosuppressant. It has inhibitory effects on lymphocyte kinase (IC50 is 0.05 μmol/L), and it also inhibits mixed lymphocyte response (IC50 is 0.009 μmol/L). 83 μg/mL of Lymphostin has no effect on the gram-positive bacteria and negative bacteria.
Specification
| Synonyms | N-Acetyl-4-(3-methoxyacryloyl)pyrrolo[4,3,2-de]quinoline-6,8-diamine; Antibiotic LK6A |
| IUPAC Name | N-[11-amino-6-[(E)-3-methoxyprop-2-enoyl]-2,7-diazatricyclo[6.3.1.04,12]dodeca-1,3,5,8(12),10-pentaen-9-ylidene]acetamide |
| Canonical SMILES | CC(=O)N=C1C=C(C2=NC=C3C2=C1NC(=C3)C(=O)C=COC)N |
| InChI | InChI=1S/C16H14N4O3/c1-8(21)19-12-6-10(17)15-14-9(7-18-15)5-11(20-16(12)14)13(22)3-4-23-2/h3-7,20H,17H2,1-2H3/b4-3+,19-12? |
| InChI Key | XAWNGCSUZLFAOC-JIBLKSCZSA-N |
Properties
| Appearance | Orange Powder |
| Melting Point | 275-277°C |
| Solubility | Soluble in Acetonitrile, Methanol |
Reference Reading
1. Discovery and assembly-line biosynthesis of the lymphostin pyrroloquinoline alkaloid family of mTOR inhibitors in Salinispora bacteria
Akimasa Miyanaga, Jeffrey E Janso, Leonard McDonald, Min He, Hongbo Liu, Laurel Barbieri, Alessandra S Eustáquio, Elisha N Fielding, Guy T Carter, Paul R Jensen, Xidong Feng, Margaret Leighton, Frank E Koehn, Bradley S Moore J Am Chem Soc. 2011 Aug 31;133(34):13311-3. doi: 10.1021/ja205655w. Epub 2011 Aug 9.
The pyrroloquinoline alkaloid family of natural products, which includes the immunosuppressant lymphostin, has long been postulated to arise from tryptophan. We now report the molecular basis of lymphostin biosynthesis in three marine Salinispora species that maintain conserved biosynthetic gene clusters harboring a hybrid nonribosomal peptide synthetase-polyketide synthase that is central to lymphostin assembly. Through a series of experiments involving gene mutations, stable isotope profiling, and natural product discovery, we report the assembly-line biosynthesis of lymphostin and nine new analogues that exhibit potent mTOR inhibitory activity.
2. Biosynthetic Pathway Connects Cryptic Ribosomally Synthesized Posttranslationally Modified Peptide Genes with Pyrroloquinoline Alkaloids
Peter A Jordan, Bradley S Moore Cell Chem Biol. 2016 Dec 22;23(12):1504-1514. doi: 10.1016/j.chembiol.2016.10.009. Epub 2016 Nov 17.
In an era where natural product biosynthetic gene clusters can be rapidly identified from sequenced genomes, it is unusual for the biosynthesis of an entire natural product class to remain unknown. Yet, the genetic determinates for pyrroloquinoline alkaloid biosynthesis have remained obscure despite their abundance and deceptive structural simplicity. In this work, we have identified the biosynthetic gene cluster for ammosamides A-C, pyrroloquinoline alkaloids from Streptomyces sp. CNR-698. Through direct cloning, heterologous expression and gene deletions we have validated the ammosamide biosynthetic gene cluster and demonstrated that these seemingly simple molecules are derived from a surprisingly complex set of biosynthetic genes that are also found in the biosynthesis of lymphostin, a structurally related pyrroloquinoline alkaloid from Salinispora and Streptomyces. Our results implicate a conserved set of genes driving pyrroloquinoline biosynthesis that consist of genes frequently associated with ribosomal peptide natural product biosynthesis, and whose exact biochemical role remains enigmatic.
3. Total syntheses of polyketide-derived bioactive natural products
Kuniaki Tatsuta, Seijiro Hosokawa Chem Rec. 2006;6(4):217-33. doi: 10.1002/tcr.20084.
Recent progress of total syntheses in our laboratory has been described along with our background and methodologies. The target bioactive polyketides are classified into three categories according to their structures: (i) lactone-fused polycyclic compounds [(+)-cochleamycin A, (+)-tubelactomicin A, and (-)-tetrodecamycin], (ii) aromatic compounds [(-)-tetracycline, (-)-BE-54238B, lymphostin, and (-)-lagunamycin], and (iii) acyclic polyketides [xanthocillin X dimethylether, (+)-trichostatin D, and (+)-actinopyrone A]. Features of the total syntheses are described. Original methodologies have been developed and applied to construct the inherent structures of the target molecules. Most syntheses cited herein are the first total syntheses, and the absolute structures of the target molecules have been determined.
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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 ╳
