Angustmycin A
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-00690 |
| CAS | 2004-04-8 |
| Molecular Weight | 279.25 |
| Molecular Formula | C11H13N5O4 |
| Purity | ≥95% |
Online Inquiry
Description
It is produced by the strain of Streptomyces hygroscopicus var. angustmyceticus. It has anti-gram-positive bacteria and mycobacterium activity.
Specification
| Synonyms | decoyinine; Decoyinin; Antibiotic A14; 9-(6-Deoxy-beta-D-erythro-hex-5-en-2-ulofuranosyl)-9H-purin-6-amine; 9-(6-Deoxy-beta-D-erythro-hex-5-enulofuranosyl)adenine; 9-(Tetrahydro-3,4-dihydroxy-2-(hydroxymethyl)-5-methylene-2-furyl)adenine |
| IUPAC Name | (2R,3R,4S)-2-(6-aminopurin-9-yl)-2-(hydroxymethyl)-5-methylideneoxolane-3,4-diol |
| Canonical SMILES | C=C1C(C(C(O1)(CO)N2C=NC3=C(N=CN=C32)N)O)O |
| InChI | InChI=1S/C11H13N5O4/c1-5-7(18)8(19)11(2-17,20-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-4,7-8,17-19H,1-2H2,(H2,12,13,14)/t7-,8-,11-/m1/s1 |
| InChI Key | UZSSGAOAYPICBZ-SOCHQFKDSA-N |
Properties
| Appearance | Colorless Acicular Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; neoplastics (Tumor); mycobacteria |
| Boiling Point | 639.8±65.0 °C (Predicted) |
| Melting Point | 198-200 °C |
| Density | 1.870±0.10 g/cm3 (Predicted) |
| Solubility | Soluble in Methanol, Water, DMF |
Reference Reading
1. Synthesis and biological studies of unsaturated acyclonucleoside analogues of S-adenosyl-L-homocysteine hydrolase inhibitors
A Hasan, P C Srivastava J Med Chem. 1992 Apr 17;35(8):1435-9. doi: 10.1021/jm00086a012.
The design, synthesis, and biological evaluation of several unsaturated acyclonucleosides related to augustmycin A are described. The (propargyloxy)methyl acyclonucleoside analogues of 6-chloropurine, adenine, 6-methoxypurine, hypoxanthine, 6-mercaptopurine, and azathioprine have been prepared. The 9-[(propargyloxy)methyl]adenine (5) and 9-[(propargyloxy)methyl]hypoxanthine (12) analogues were converted to the corresponding 5'-tributylstannyl intermediates (9 and 13), respectively, which gave 9-[[[(Z)-5-iodo-5-propenyl]oxy]methyl]adenine (10) and 9-[[[(Z)-5-iodo-5-propenyl]oxy]methyl]hypoxanthine (14), respectively, after iododestannylation. The [125I]-radiolabeled congeners of 10 and 14 were prepared as potential metabolic markers. Among the unsaturated acyclonucleosides tested, 9-[(propargyloxy)methyl]-6-chloropurine (3), 9-[(propargyloxy)methyl]-6-mercaptopurine (15), 9-[(propargyloxy)methyl]azathioprine (17), and angustmycin A analogue 10 showed inhibition of cancer cell growth, but only at a minimal level, and 17 also showed 14% cancer cell death in vitro. Compound 10 provided approximately 50% protection against HIV at 10(-4) M concentrations. Biodistribution results of [125I]-10 in mice indicate that compound 10 is readily metabolized via deiodination in vivo, possibly by serving as a substrate for the enzyme S-adenosyl-L-homocysteine hydrolase.
2. Efficient biosynthesis of nucleoside cytokinin angustmycin A containing an unusual sugar system
Le Yu, Wenting Zhou, Yixuan She, Hongmin Ma, You-Sheng Cai, Ming Jiang, Zixin Deng, Neil P J Price, Wenqing Chen Nat Commun. 2021 Nov 17;12(1):6633. doi: 10.1038/s41467-021-26928-y.
Angustmycin A has anti-mycobacterial and cytokinin activities, and contains an intriguing structure in which an unusual sugar with C5'-C6' dehydration is linked to adenine via an N-glycosidic bond. However, the logic underlying the biosynthesis of this molecule has long remained obscure. Here, we address angustmycin A biosynthesis by the full deciphering of its pathway. We demonstrate that AgmD, C, A, E, and B function as D-allulose 6-phosphate 3-epimerase, D-allulose 6-phosphate pyrophosphokinase, adenine phosphoallulosyltransferase, phosphoribohydrolase, and phosphatase, respectively, and that these collaboratively catalyze the relay reactions to biosynthesize angustmycin C. Additionally, we provide evidence that AgmF is a noncanonical dehydratase for the final step to angustmycin A via a self-sufficient strategy for cofactor recycling. Finally, we have reconstituted the entire six-enzyme pathway in vitro and in E. coli leading to angustmycin A production. These results expand the enzymatic repertoire regarding natural product biosynthesis, and also open the way for rational and rapid discovery of other angustmycin related antibiotics.
3. Pharmacological targeting of guanosine monophosphate synthase suppresses melanoma cell invasion and tumorigenicity
A Bianchi-Smiraglia, J A Wawrzyniak, A Bagati, E K Marvin, J Ackroyd, S Moparthy, W Bshara, E E Fink, C E Foley, G E Morozevich, A E Berman, D S Shewach, M A Nikiforov Cell Death Differ. 2015 Nov;22(11):1858-64. doi: 10.1038/cdd.2015.47. Epub 2015 Apr 24.
Malignant melanoma possesses one of the highest metastatic potentials among human cancers. Acquisition of invasive phenotypes is a prerequisite for melanoma metastases. Elucidation of the molecular mechanisms underlying melanoma invasion will greatly enhance the design of novel agents for melanoma therapeutic intervention. Here, we report that guanosine monophosphate synthase (GMPS), an enzyme required for the de novo biosynthesis of GMP, has a major role in invasion and tumorigenicity of cells derived from either BRAF(V600E) or NRAS(Q61R) human metastatic melanomas. Moreover, GMPS levels are increased in metastatic human melanoma specimens compared with primary melanomas arguing that GMPS is an attractive candidate for anti-melanoma therapy. Accordingly, for the first time we demonstrate that angustmycin A, a nucleoside-analog inhibitor of GMPS produced by Streptomyces hygroscopius efficiently suppresses melanoma cell invasion in vitro and tumorigenicity in immunocompromised mice. Our data identify GMPS as a powerful driver of melanoma cell invasion and warrant further investigation of angustmycin A as a novel anti-melanoma agent.
Recommended Products
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-02614 | Nystatin | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
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 ╳
