Respinomycin A2

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Respinomycin A2
Category Antibiotics
Catalog number BBF-02186
CAS 151233-04-4
Molecular Weight 842.92
Molecular Formula C43H58N2O15

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Description

Respinomycin A2 is produced by the strain of Str. xanthocidicus RK-483 and it causes the differentiation of leukemic K-562 cells.

Specification

Synonyms 2,6-Epoxy-2H-naphthaceno(1,2-b)oxocin-9,16-dione, 3,4,5,6,11,12,13,14-octahydro-5-((3-amino-2,3,6-trideoxy-4-O-(6-deoxy-3-C-methyl-2-O-methyl-alpha-mannopyranosyl)-3-C-methyl-beta-ribo-hexopyranosyl)oxy)-6,12-dimethyl-4-(dimethylamino)-13-methoxy-3,12,15-trihydroxy-, (2-alpha,3-beta,4-alpha,5-alpha,6-alpha,12-beta,13-alpha)-(+)-
IUPAC Name 24-[4-amino-5-(4,5-dihydroxy-3-methoxy-4,6-dimethyloxan-2-yl)oxy-4,6-dimethyloxan-2-yl]oxy-23-(dimethylamino)-11,15,22-trihydroxy-12-methoxy-1,11-dimethyl-20,25-dioxahexacyclo[19.3.1.02,19.05,18.07,16.09,14]pentacosa-2(19),3,5(18),7(16),8,14-hexaene-6,17-dione
Canonical SMILES CC1C(C(C(C(O1)OC2C(OC(CC2(C)N)OC3C(C(C4OC5=C(C3(O4)C)C=CC6=C5C(=O)C7=C(C6=O)C=C8CC(C(CC8=C7O)OC)(C)O)O)N(C)C)C)OC)(C)O)O
InChI InChI=1S/C43H58N2O15/c1-17-34(50)42(5,52)37(54-10)39(56-17)59-35-18(2)55-25(16-40(35,3)44)57-36-28(45(7)8)32(49)38-58-33-23(43(36,6)60-38)12-11-20-27(33)31(48)26-22(29(20)46)13-19-15-41(4,51)24(53-9)14-21(19)30(26)47/h11-13,17-18,24-25,28,32,34-39,47,49-52H,14-16,44H2,1-10H3
InChI Key RMEJXXRMYWGEAP-UHFFFAOYSA-N

Properties

Appearance Yellow Powder
Antibiotic Activity Spectrum neoplastics (Tumor)
Melting Point >202°C
Density 1.45±0.1 g/cm3

Reference Reading

1. Respinomycins A1, A2 B, C and D, a novel group of anthracycline antibiotics. I. Taxonomy, fermentation, isolation and biological activities
M Ubukata, H Osada, T Kudo, K Isono J Antibiot (Tokyo). 1993 Jun;46(6):936-41. doi: 10.7164/antibiotics.46.936.
Respinomycins are a novel group of anthracycline antibiotics produced by Streptomyces xanthocidicus. Respinomycins A1, A2, B, C and D were isolated by EtOAc extraction, silica gel column chromatography, centrifugal partition chromatography and preparative silica gel thin layer chromatography. Respinomycins A1 and A2 induced the terminal differentiation of human leukemia K-562 cells.
2. Respinomycins A1, A2, B, C and D, a novel group of anthracycline antibiotics. II. Physico-chemical properties and structure elucidation
M Ubukata, J Uzawa, H Osada, K Isono J Antibiot (Tokyo). 1993 Jun;46(6):942-51. doi: 10.7164/antibiotics.46.942.
Respinomycins A1, A2, B, C and D were revealed to be novel anthracycline antibiotics with molecular formulae of C51H72N2O20, C43H58N2O15, C35H43NO14, C36H45NO14 and C51H70N2O22, respectively. Their structures were determined by means of 1H-1H COSY, 13C-1H COSY and HMBC spectra. The structure of the aglycone of respinomycins was unambiguously determined by LSPD experiments and NOESY. The common skeleton of respinomycins is a new type and is distinguished from that of the nogalamycin group.

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