Angolamycin
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| Category | Antibiotics |
| Catalog number | BBF-00687 |
| CAS | 1402-83-1 |
| Molecular Weight | 916.10 |
| Molecular Formula | C46H77NO17 |
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Description
It is produced by the strain of Streptomyces eurythermus. It has anti-gram-positive bacteria activity and has effect on Mycoplasma pneumoniae Mac.
Specification
| Synonyms | Sincomycin A; Angolamycin, BRN 6045489; LS-19552; 2-[(14E)-9-[5-(4,5-dihydroxy-4,6-dimethyl-tetrahydropyran-2-yl)oxy-4-(dimethylamino)-6-methyl-tetrahydropyran-2-yl]oxy-3-ethyl-7-hydroxy-2-[(5-hydroxy-3,4-dimethoxy-6-methyl-tetrahydropyran-2-yl)oxymethyl]-8,12,16-trimethyl-5,13-dioxo-4,17-dioxabicyclo[14.1.0]heptadec-14-en-10-yl]acetaldehyde |
| IUPAC Name | 2-[(14E)-9-[5-(4,5-dihydroxy-4,6-dimethyloxan-2-yl)oxy-4-(dimethylamino)-6-methyloxan-2-yl]oxy-3-ethyl-7-hydroxy-2-[(5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl)oxymethyl]-8,12,16-trimethyl-5,13-dioxo-4,17-dioxabicyclo[14.1.0]heptadec-14-en-10-yl]acetaldehyde |
| Canonical SMILES | CCC1C(C2C(O2)(C=CC(=O)C(CC(C(C(C(CC(=O)O1)O)C)OC3CC(C(C(O3)C)OC4CC(C(C(O4)C)O)(C)O)N(C)C)CC=O)C)C)COC5C(C(C(C(O5)C)O)OC)OC |
| InChI | InChI=1S/C46H77NO17/c1-13-33-29(22-57-44-41(56-12)40(55-11)37(52)25(4)60-44)43-46(8,64-43)16-14-31(49)23(2)18-28(15-17-48)38(24(3)32(50)20-34(51)61-33)62-35-19-30(47(9)10)39(26(5)58-35)63-36-21-45(7,54)42(53)27(6)59-36/h14,16-17,23-30,32-33,35-44,50,52-54H,13,15,18-22H2,1-12H3/b16-14+ |
| InChI Key | KZXDKUWSAVUSKI-JQIJEIRASA-N |
Properties
| Appearance | Colorless Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycoplasma |
| Boiling Point | 959.5 °C at 760 mmHg |
| Melting Point | 131-134 °C |
| Density | 1.250 g/cm3 |
| Solubility | Soluble in Ethanol, Chloroform |
Reference Reading
1. Isolation and structure elucidation of new antibiotics related to angolamycin
J Kádár-Pauncz, B Podányi, G Horváth J Antibiot (Tokyo). 1992 Aug;45(8):1231-8. doi: 10.7164/antibiotics.45.1231.
Angolamycin (1) and two novel analogues (2 and 3) were isolated from the culture broth of a Streptomyces strain. NMR and MS analysis proved that 2 is the 18-dihydro-, while 3 is the 18-deoxo-18-dihydro derivative of angolamycin. Full experimental assignment of the 1H and the 13C NMR spectra of these compounds was obtained from 1D and 2D chemical shift correlation measurements. Compounds 2 and 3 are less potent antibiotics than angolamycin.
2. Deepoxidation of 16-membered epoxyenone macrolide antibiotics. III. In vitro and in vivo evaluation of deepoxidation products of carbomycin A, deltamycin A1, 4"-phenylacetyldeltamycin, angolamycin and rosamicin
M Sakamoto, Y Mutoh, Y Fukagawa, T Ishikura, J Lein J Antibiot (Tokyo). 1984 Feb;37(2):130-5. doi: 10.7164/antibiotics.37.130.
Deepoxidation products P1, P2 and P3 of carbomycin A, deltamycin A1 and 4"-phenylacetyldeltamycin showed high in vitro antibacterial and antimycoplasmal activities which were comparable to those of the respective parent compounds. By contrast, the in vitro antimicrobial potencies of angolamycin P1 and rosamicin P1 were about ten-fold lower than those of the parent macrolides. In mice, the increase in the plasma levels of the epoxyenone macrolides due to deepoxidation was highly significant with the P1, P2 and P3 derivatives of carbomycin A and 4"-phenylacetyldeltamycin, whereas angolamycin P1 gave a moderately-improved plasma level compared with angolamycin.
3. Deepoxidation of 16-membered epoxyenone macrolide antibiotics. II. Chemical deepoxidation by dissolving metal reduction
Y Mutoh, Y Shimauchi, Y Fukagawa, T Ishikura, J Lein J Antibiot (Tokyo). 1984 Feb;37(2):127-9. doi: 10.7164/antibiotics.37.127.
16-Membered epoxyenone macrolide antibiotics were reductively deepoxidized with dissolving metals such as zinc. Angolamycin and rosamicin which have a methyl substituent at C-12 in the epoxyenone structure were deepoxidized, but not isomerized further to the geometric isomers P2 and P3.
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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 ╳
