Angustmycin C
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| Category | Antibiotics |
| Catalog number | BBF-00691 |
| CAS | 1874-54-0 |
| Molecular Weight | 297.27 |
| Molecular Formula | C11H15N5O5 |
| Purity | ≥98% |
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Description
It is produced by the strain of Streptomyces hygroscopicus var. angustmyceticus. It has anti-gram-positive bacteria and mycobacterium activity, and has an inhibitory effect on Walker cancer 256 in rats and adenocarcinoma Ca755 in mice.
Specification
| Synonyms | Angustmycin C; NSC 53104; Psicofuranosyladenine; 1'-(Hydroxymethyl)adenosine; (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-2,5-bis(hydroxymethyl)oxolane-3,4-diol |
| IUPAC Name | (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-2,5-bis(hydroxymethyl)oxolane-3,4-diol |
| Canonical SMILES | C1=NC(=C2C(=N1)N(C=N2)C3(C(C(C(O3)CO)O)O)CO)N |
| InChI | InChI=1S/C11H15N5O5/c12-9-6-10(14-3-13-9)16(4-15-6)11(2-18)8(20)7(19)5(1-17)21-11/h3-5,7-8,17-20H,1-2H2,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1 |
| InChI Key | BNZYRKVSCLSXSJ-IOSLPCCCSA-N |
Properties
| Appearance | Solid Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; neoplastics (Tumor); mycobacteria |
| Boiling Point | 720.1±70.0 °C (Predicted) |
| Melting Point | 202-294 °C (dec.) |
| Density | 2.020±0.10 g/cm3 (Predicted) |
| Solubility | Soluble in 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. Ring opening of nucleoside 1',2'-epoxides with organoaluminum reagents: stereoselective entry to ribonucleosides branched at the anomeric position
Hiromichi Tanaka, Yutaka Kubota, Kazuhiro Haraguchi J Org Chem . 2004 Mar 19;69(6):1831-6. doi: 10.1021/jo030262u.
Epoxidation of 3',5'-O-(di-tert-butylsilylene)-1',2'-unsaturated uridine (11) with dimethyldioxirane proceeded from the alpha-face to give the 1',2'-alpha-epoxide 12. Upon reacting with organoaluminum reagents, the 1',2'-alpha-epoxide 12 underwent preferential syn-opening of the epoxide ring to yield the beta-anomers of 1'-methyl- (13beta), 1'-ethyl- (14beta), 1'-isobutyl- (15beta), 1'-ethynyl- (16beta), 1'-vinyl- (17beta), and 1'-phenyl- (18beta) uridine derivatives, although the corresponding alpha-anomers were also formed except for the reaction with triphenylaluminum. It was found, however, that protection of the N(3)-position of 11 either with a benzyloxymethyl or benzoyl group led to the exclusive formation of the desired beta-anomers. A possible explanation for the observed stereochemical outcome is presented. A similar strategy was found to be applicable to the synthesis of 1'-branched adenosine analogues, which include protected angustmycin C (37).
3. Bacillus subtilis CodY represses early-stationary-phase genes by sensing GTP levels
P Serror, M Ratnayake-Lecamwasam, A L Sonenshein, K W Wong Genes Dev . 2001 May 1;15(9):1093-103. doi: 10.1101/gad.874201.
CodY, a highly conserved protein in the low G + C, gram-positive bacteria, regulates the expression of many Bacillus subtilis genes that are induced as cells make the transition from rapid exponential growth to stationary phase and sporulation. This transition has been associated with a transient drop in the intracellular pool of GTP. Many stationary-phase genes are also induced during exponential-growth phase by treatment of cells with decoyinine, a GMP synthetase inhibitor. The effect of decoyinine on an early-stationary-phase gene is shown here to be mediated through CodY and to reflect a reduction in guanine nucleotide accumulation. CodY proved to bind GTP in vitro. Moreover, CodY-mediated repression of target promoters was dependent on a high concentration of GTP, comparable to that found in rapidly growing exponential-phase cells. Because a codY-null mutant was able to sporulate under conditions of nutrient excess, CodY also appears to be a critical factor that normally prevents sporulation under such conditions. Thus, B. subtilis CodY is a novel GTP-binding protein that senses the intracellular GTP concentration as an indicator of nutritional conditions and regulates the transcription of early-stationary-phase and sporulation genes, allowing the cell to adapt to nutrient limitation.
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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 ╳
