Seldomycin 2

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Seldomycin 2
Category Antibiotics
Catalog number BBF-02897
CAS 54333-78-7
Molecular Weight 306.36
Molecular Formula C12H26N4O5

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Description

Seldomycin 2 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 36-60 mg/kg (abdominal infection in mice, intravenous administration).

Specification

Synonyms 4'-Deoxyneamine; Seldomycin factor 2; Antibiotic XK 88-2; XK 88-2; D-Streptamine, 2-deoxy-4-O-(2,6-diamino-2,4,6-trideoxy-alpha-D-xylo-hexopyranosyl)-
IUPAC Name (1S,2R,3R,4S,6R)-4,6-diamino-3-[(2R,3R,4S,6S)-3-amino-6-(aminomethyl)-4-hydroxyoxan-2-yl]oxycyclohexane-1,2-diol
Canonical SMILES C1C(OC(C(C1O)N)OC2C(CC(C(C2O)O)N)N)CN
InChI InChI=1S/C12H26N4O5/c13-3-4-1-7(17)8(16)12(20-4)21-11-6(15)2-5(14)9(18)10(11)19/h4-12,17-19H,1-3,13-16H2/t4-,5+,6-,7-,8+,9-,10+,11+,12+/m0/s1
InChI Key NOBINJIDZDKGAE-GVYSDAGYSA-N

Properties

Appearance White Amorphous Powder
Boiling Point 548.3°C at 760 mmHg
Melting Point 225-250°C (dec.)
Density 1.42 g/cm3
Solubility Soluble in Water

Reference Reading

1. A new aminoglycoside antibiotic complex--the seldomycins. III. The structures of seldomycin factors 1 and 2+
R S Egan, A C Sinclair, R L De Vault, J B McAlpine, S L Mueller, P C Goodley, R S Stanaszek, M Cirovic, R J Mauritz, L A Mitscher, K Shirahata, S Sato, T Iida J Antibiot (Tokyo). 1977 Jan;30(1):31-8. doi: 10.7164/antibiotics.30.31.
The structures of seldomycin factors 1 and 2 have been determined by consideration of chemical degradation and spectral properties. Factor 1, also known as XK-88-1, is shown to be 6-O-(2-amino-2-deoxy-alpha-D-xylopyranosyl) paromamine (1) and factor 2, also known as XK-88-2, is shown to be 4'-deoxy-neamine (2). Mass spectral evidence has been obtained that suggests the most probable structure for seldomycin factor 3, also known as XK-88-3, is 6'-amino-6'-deoxyseldomycin factor 1 (12).
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. 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.

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