Arugomycin
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| Category | Antibiotics |
| Catalog number | BBF-00094 |
| CAS | 88465-80-9 |
| Molecular Weight | 1693.73 |
| Molecular Formula | C80H112N2O37 |
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Description
Arugomycin is an onion ring antibiotic produced by Streptomyces violochromogenes 1098-AV2. It has anti-Gram-positive bacteria activity, and its anti-Ehrlich ascites cancer activity is similar to that of Acalamycin, but lower than that of Doxorubicin.
Specification
| Synonyms | 2,6-Epoxy-2H-naphthaceno(1,2-b)oxocin, arugomycin deriv. |
| IUPAC Name | (E)-4-[6-[6-[6-[6-[[23-(dimethylamino)-4,8,12,22-tetrahydroxy-24-[4-hydroxy-5-[5-(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy-4,6-dimethyl-4-nitrooxan-2-yl]oxy-6-methyloxan-2-yl]oxy-13-methoxycarbonyl-1,12-dimethyl-6,17-dioxo-20,25-dioxahexacyclo[19.3.1.02,19.05,18.07,16.09,14]pentacosa-2,4,7(16),8,14,18-hexaen-10-yl]oxy]-4-methoxy-2-methyloxan-3-yl]oxy-4-hydroxy-2-methyloxan-3-yl]oxy-4-methoxy-2-methyloxan-3-yl]oxy-4-methoxy-2-methyloxan-3-yl]oxy-4-oxobut-2-enoic acid |
| Canonical SMILES | CC1C(C(CC(O1)OC2C(OC(CC2(C)[N+](=O)[O-])OC3C(OC(CC3O)OC4C(C(C5OC6=C7C(=C(C=C6C4(O5)C)O)C(=O)C8=C(C7=O)C=C9C(C(CC(C9=C8O)OC1CC(C(C(O1)C)OC1CC(C(C(O1)C)OC1CC(C(C(O1)C)OC1CC(C(C(O1)C)OC(=O)C=CC(=O)O)OC)OC)O)OC)(C)O)C(=O)OC)O)N(C)C)C)C)OC)O |
| InChI | InChI=1S/C80H112N2O37/c1-30-63(89)43(98-13)24-55(103-30)116-74-36(7)109-56(29-78(74,8)82(96)97)115-69-32(3)105-51(23-42(69)85)117-75-62(81(11)12)67(93)77-118-73-39(80(75,10)119-77)21-40(83)59-60(73)64(90)38-20-37-57(65(91)58(38)66(59)92)47(28-79(9,95)61(37)76(94)102-17)110-52-25-45(100-15)71(34(5)106-52)113-50-22-41(84)68(31(2)104-50)112-53-27-46(101-16)72(35(6)108-53)114-54-26-44(99-14)70(33(4)107-54)111-49(88)19-18-48(86)87/h18-21,30-36,41-47,50-56,61-63,67-72,74-75,77,83-85,89,91,93,95H,22-29H2,1-17H3,(H,86,87)/b19-18+ |
| InChI Key | MWGPOKWHXRTZII-VHEBQXMUSA-N |
Properties
| Appearance | Orange Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; neoplastics (Tumor) |
| Melting Point | 208-212°C (dec.) |
Reference Reading
1. Reagent-Controlled α-Selective Dehydrative Glycosylation of 2,6-Dideoxy Sugars: Construction of the Arugomycin Tetrasaccharide
Joseph R Romeo, Luca McDermott, Clay S Bennett Org Lett. 2020 May 1;22(9):3649-3654. doi: 10.1021/acs.orglett.0c01153. Epub 2020 Apr 13.
The first synthesis of the tetrasaccharide fragment of the anthracycline natural product Arugomycin is described. A reagent controlled dehydrative glycosylation method involving cyclopropenium activation was utilized to synthesize the α-linkages with complete anomeric selectivity. The synthesis was completed in 20 total steps, and in 2.5% overall yield with a longest linear sequence of 15 steps.
2. Anthracycline antibiotic arugomycin binds in both grooves of the DNA helix simultaneously: an NMR and molecular modelling study
M S Searle, W Bicknell, L P Wakelin, W A Denny Nucleic Acids Res. 1991 Jun 11;19(11):2897-906. doi: 10.1093/nar/19.11.2897.
Perturbations to the 1H and 31P chemical shifts of DNA resonances together with twenty-four intermolecular nuclear Overhauser effects show that the anthracycline antibiotic arugomycin intercalates between the basepairs of the hexamer duplex d(5'-GCATGC)2 at the 5'-CpA and 5'-TpG binding sites. In the complex two drug molecules are bound per duplex with full retention of the dyad symmetry. Arugomycin adopts a threaded binding orientation with chains of sugars positioned in both the major and minor groove of the helix simultaneously. The complex is stabilized by hydrogen bonding, electrostatic and van der Waals interactions principally in the major groove and involving substituents on the rigidly oriented bicycloamino-glucose sugar of the antibiotic. A specific hydrogen bond is identified between the C2'-hydroxyl and the guanine N7 at the intercalation site. Together, interactions in the major groove appear to account for the intercalation specificity of arugomycin that requires both a guanine and thymine at the intercalation site. We are unable to identify any sequence specific interactions between the minor groove and the arugarose sugar (S1) which binds only weakly, through van der Walls contacts, over the d(GCA).d(TGC) trinucleotide sequence. The data indicate that the sugar chains of arugomycin are flexible and play little part in the interaction of the antibiotic with DNA. The intensity of sequential internucleotide NOEs identifies the intercalation site as being assymmetric. A family of conformers computed using restrained energy minimisation and molecular dynamics indicate that basepair buckling is a feature of the anthracycline intercalation site that may serve to maximise intermolecular van der Waals interactions by wrapping the basepairs around the antibiotic chromophore.
3. Viriplanin A, a new anthracycline antibiotic of the nogalamycin group. II. The structure of a novel hydroxyamino sugar from reduced viriplanin A
R Kind, K Hütter, A Zeeck, K Schmidt-Bäse, E Egert J Antibiot (Tokyo). 1989 Jan;42(1):7-13. doi: 10.7164/antibiotics.42.7.
Methyl 2,3,6-trideoxy-3-hydroxyamino-3-C-methyl-alpha-D-ribo-hexopyranoside+ ++ (2) and the corresponding amino sugar (4) were isolated from reduced viriplanin A by acidic methanolysis and esterified to the di-p-bromobenzoates (3 and 5), respectively. The absolute configuration of crystalline 3 was determined by X-ray analysis to be alpha-D. This result could be confirmed by oxidation of 2 to methyl alpha-D-decilonitroside (6) and from the CD spectra of 3 and 5. Thus, the nitrogen-containing sugars of viriplanin A and probably those of decilorubicin and arugomycin belong to the D-series.
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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 ╳
