Seldomycin 3
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| Category | Antibiotics |
| Catalog number | BBF-02898 |
| CAS | 56276-05-2 |
| Molecular Weight | 453.49 |
| Molecular Formula | C17H35N5O9 |
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Description
Seldomycin 3 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)).
Specification
| Synonyms | 6-O-(2-Amino-2-deoxy-α-D-xylopyranosyl)-4-O-(2,6-diamino-2,6-dideoxy-α-D-glucopyranosyl)-2-deoxy-D-streptamine; Seldomycin factor-3; Xk-88-3; Antibiotic XK-88-3 |
| IUPAC Name | (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-3-[(2R,3R,4R,5R)-3-amino-4,5-dihydroxyoxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4-diol |
| Canonical SMILES | C1C(C(C(C(C1N)OC2C(C(C(C(O2)CN)O)O)N)O)OC3C(C(C(CO3)O)O)N)N |
| InChI | InChI=1S/C17H35N5O9/c18-2-7-11(25)12(26)9(22)17(29-7)31-15-5(20)1-4(19)14(13(15)27)30-16-8(21)10(24)6(23)3-28-16/h4-17,23-27H,1-3,18-22H2/t4-,5+,6-,7-,8-,9-,10+,11-,12-,13-,14+,15-,16-,17-/m1/s1 |
| InChI Key | ZAOUGJBZKPMBDW-PZQDWFEXSA-N |
Properties
| Appearance | White Amorphous Powder |
| Melting Point | 215-240°C (dec.) |
| Solubility | Soluble in Water, Methanol |
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. aph(3')-IIb, a gene encoding an aminoglycoside-modifying enzyme, is under the positive control of surrogate regulator HpaA
Lin Zeng, Shouguang Jin Antimicrob Agents Chemother. 2003 Dec;47(12):3867-76. doi: 10.1128/AAC.47.12.3867-3876.2003.
Pseudomonas aeruginosa harbors a chromosomal aminoglycoside phosphotransferase gene, aph(3')-IIb, which confers P. aeruginosa resistance to several important aminoglycoside antibiotics, including kanamycin A and B, neomycin B and C, butirosin, and seldomycin F5. The aph(3')-IIb gene has been found to be regulated by an AraC-type transcriptional regulator (HpaA) encoded by a gene located upstream of the aph(3')-IIb gene. In the presence of 4-hydroxyphenylacetic acid (4-HPA), HpaA activates the expression of aph(3')-IIb as well as that of the hpa regulon which encodes metabolic enzymes for the utilization of 4-HPA. hpaA and aph(3')-IIb form an operon, and in response to the presence of 4-HPA, the wild-type P. aeruginosa strain PAK (but not its hpaA mutant strain) displays increased resistance to neomycin. A survey of 39 clinical and 19 environmental isolates of P. aeruginosa demonstrated in all of them the presence of an hpaA-aph gene cluster, while 56 out of the 58 isolates are able to utilize the 4-HPA as a sole carbon source, suggesting a feature common to P. aeruginosa strains. Interestingly, a larger portion of clinical isolates than environmental isolates showed 4-HPA-induced resistance to neomycin. The aph(3')-IIb gene product is likely to function as a metabolic enzyme which has a cross-reactivity with aminoglycosides. These findings provide new insight into the possible mechanism of P. aeruginosa antibiotic resistance.
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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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 ╳
