Seldomycin 5

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Seldomycin 5
Category Antibiotics
Catalog number BBF-02899
CAS 56276-26-7
Molecular Weight 450.53
Molecular Formula C18H38N6O7

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Description

Seldomycin 5 is an aminoglycoside antibiotic produced by the strain of Str. hofunensis nor. sp.. It has a broad spectrum of antimicrobial activity, and Seldomycin F5 has the strongest antimicrobial activity. It is cross-resistant to E. coli with aminoglycoside antibiotic passivation enzyme (such as APH (3')-Ⅰ, APH(3')-II, AAC(6'), AAC(2)). ED50 is 7.5-15 mg/kg (abdominal infection in mice, intravenous administration).

Specification

Synonyms 6-O-(2,3-Diamino-4-O-methyl-2,3-dideoxy-α-D-xylopyranosyl)-4-O-(2,6-diamino-2,4,6-trideoxy-α-D-xylo-hexopyranosyl)-2-deoxy-D-streptamine; Seldomycin factor-5; D-Streptamine, O-2,3-diamino-2,3-dideoxy-4-o-methyl-alpha-D-xylopyranosyl-(1-6)-o-(2,6-diamino-2,4,6-trideoxy-alpha-D-xylo-hexopyranosyl-(1-4))-2-deoxy-; Xk-88-5; Antibiotic XK-88-5
IUPAC Name (2R,3R,4S,6S)-3-amino-6-(aminomethyl)-2-[(1R,2R,3S,4R,6S)-4,6-diamino-3-[(2R,3R,4R,5S)-3,4-diamino-5-methoxyoxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxan-4-ol
Canonical SMILES COC1COC(C(C1N)N)OC2C(CC(C(C2O)OC3C(C(CC(O3)CN)O)N)N)N
InChI InChI=1S/C18H38N6O7/c1-27-10-5-28-17(13(24)12(10)23)30-15-7(20)3-8(21)16(14(15)26)31-18-11(22)9(25)2-6(4-19)29-18/h6-18,25-26H,2-5,19-24H2,1H3/t6-,7+,8-,9-,10+,11+,12-,13+,14+,15-,16+,17+,18+/m0/s1
InChI Key HJKXMQLJTKUBMG-BAOVJYBRSA-N

Properties

Appearance White Amorphous Powder
Boiling Point 678.6°C at 760 mmHg
Melting Point 215-240°C (dec.)
Density 1.39 g/cm3
Solubility Soluble in Water, Methanol, Ethanol

Reference Reading

1. A new aminoglycoside antibiotic complex--the seldomycins. II. Isolation, physicochemical and chromatographic properties
S Sato, S Takasawa, T Sato, M Yamamoto, R Okachi J Antibiot (Tokyo). 1977 Jan;30(1):25-30. doi: 10.7164/antibiotics.30.25.
An antibiotic complex consisting of four components, seldomycin factors 1, 2, 3 and 5 was isolated from the fermentation broth of Streptomyces hofunensis sp. nov. by use of a cationic exchange resin. After silica gel column chromatography, the purified components were characterized as new aminoglycoside antibiotics by their physicochemical, chromatographic and antimicrobial properties.
2. A new aminoglycoside antibiotic complex--the seldomycins. I. Taxonomy, fermentation and antibacterial properties
T Nara, M Yamamoto, S Takasawa, S Sato, T Sato J Antibiot (Tokyo). 1977 Jan;30(1):17-24. doi: 10.7164/antibiotics.30.17.
A soil isolate named Streptomyces hofunensis sp. nov. was found to produce seldomycin factors 1, 2, 3 and 5, new aminoglycoside antibiotics. Taxonomy of the producing organism, a study of cultural conditions for seldomycin production, and antibacterial activity of seldomycins are reported. Seldomycin factor 5 was the most active both in vitro and in vivo against gram-positive and negative bacteria.
3. Modification of seldomycin factor 5 at C-3'
R E Carney, J B McAlpine, M Jackson, R S Stanaszek, W H Washburn, M Cirovic, S L Mueller J Antibiot (Tokyo). 1978 May;31(5):441-50. doi: 10.7164/antibiotics.31.441.
Attempted removal of the 3'-hydroxyl group of seldomycin factor 5 via displacement of a sulfonate ester has led to 3'-epi-seldomycin factor 5. Removal of the hydroxyl group has been effected by the Barton procedure. The antibacterial activity of 3'-epi- and 3'-deoxyseldomycin factor 5 against various aminoglycoside-resistant strains is discussed.

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