Deltamycin A1
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| Category | Antibiotics |
| Catalog number | BBF-00807 |
| CAS | 58880-22-1 |
| Molecular Weight | 799.90 |
| Molecular Formula | C39H61NO16 |
| Purity | >98% |
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Description
Deltamycin A1 is a sixteen-membered macrolide antibiotic produced by Streptomyces deltae. Activity against Gram-positive bacteria
Specification
| Synonyms | Leucomycin V, 9-deoxy-12,13-epoxy-12,13-dihydro-9-oxo-, 3,4(sup B)-diacetate, (12S,13S)- |
| Storage | Store at -20°C |
| IUPAC Name | [(14E)-9-[5-(5-acetyloxy-4-hydroxy-4,6-dimethyloxan-2-yl)oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-8-methoxy-3,12-dimethyl-5,13-dioxo-10-(2-oxoethyl)-4,17-dioxabicyclo[14.1.0]heptadec-14-en-7-yl] acetate |
| Canonical SMILES | CC1CC(C(C(C(CC(=O)OC(CC2C(O2)C=CC1=O)C)OC(=O)C)OC)OC3C(C(C(C(O3)C)OC4CC(C(C(O4)C)OC(=O)C)(C)O)N(C)C)O)CC=O |
| InChI | InChI=1S/C39H61NO16/c1-19-15-25(13-14-41)35(36(48-10)29(52-23(5)42)17-30(45)49-20(2)16-28-27(54-28)12-11-26(19)44)56-38-33(46)32(40(8)9)34(21(3)51-38)55-31-18-39(7,47)37(22(4)50-31)53-24(6)43/h11-12,14,19-22,25,27-29,31-38,46-47H,13,15-18H2,1-10H3/b12-11+ |
| InChI Key | BSLHJKFVBDZBEO-VAWYXSNFSA-N |
Properties
| Appearance | Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 875.4°C at 760 mmHg |
| Melting Point | 201-204°C |
| Density | 1.26 g/cm3 |
| Solubility | Soluble in Methanol, Toluene |
Reference Reading
1. 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.
2. Deltamycins, new macrolide antibiotics. III. Chemical structures
Y Shimauchi, K Kubo, K Osumi, K Okamura, Y Fukagawa, T Ishikura, J Lein J Antibiot (Tokyo). 1979 Sep;32(9):878-83. doi: 10.7164/antibiotics.32.878.
The structures of deltamycins A1,A2,A3 and A4 belonging to the basic macrolide family of antibiotics were determined mainly from their spectral properties. Deltamycin A4 was identified as carbomycin A having an isovaleryl group on the mycarose moiety of the molecule. Deltamycin A1,A2 and A3 possess similarities to the structure of deltamycin A4, but they have acetyl, propionyl and n-butyryl group, respectively, in the place of isovaleryl group of deltamycin A4. These structures were confirmed by chemical synthesis from deltamycin X (4''-O-deacyldeltamycin) and the corresponding acyl chlorides.
3. Deepoxidation of 16-membered epoxyenone macrolide antibiotics. I. Microbial deepoxidation and subsequent isomerization of deltamycins A1, A2, A3, A4 (carbomycin A) and X
Y Fukagawa, Y Mutoh, T Ishikura, J Lein J Antibiot (Tokyo). 1984 Feb;37(2):118-26. doi: 10.7164/antibiotics.37.118.
Carbomycin A (deltamycin A4) was deepoxidized to carbomycin A P1 by Streptomyces halstedii subsp. deltae (a deltamycins producer), favorably under anaerobic conditions. Carbomycin A P1 was spontaneously converted to geometric isomers designated carbomycins A P2 and A P3. This type of deepoxidation and subsequent isomerization was not limited to carbomycin A, but generally occurrable in other 16-membered epoxyenone macrolide compounds. Many bacteria and actinomycetes were also found to have an ability to deepoxidize deltamycins reductively. The chemical structures of carbomycins A P1, A P2 and A P3 were elucidated as shown in Fig. 3.
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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 ╳
