2-Hydroxygentamicin C1
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| Category | Antibiotics |
| Catalog number | BBF-01725 |
| CAS | 60609-40-7 |
| Molecular Weight | 493.59 |
| Molecular Formula | C21H43N5O8 |
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Description
2-Hydroxygentamicin C1 is an antibiotic of the gentamicin group produced by the fermentation of Micromonospora purpurea VI b and VI b-3P in the presence of deoxystreptamine and 2,3,6/3,5-pentahydroxycyclohexanone. It has anti-gram-positive and negative bacteria activity.
Specification
| IUPAC Name | 2-[2,4-diamino-5-[3-amino-6-[1-(methylamino)ethyl]oxan-2-yl]oxy-3,6-dihydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol |
| Canonical SMILES | CC(C1CCC(C(O1)OC2C(C(C(C(C2O)OC3C(C(C(CO3)(C)O)NC)O)N)O)N)N)NC |
| InChI | InChI=1S/C21H43N5O8/c1-8(25-3)10-6-5-9(22)19(32-10)33-16-11(23)13(27)12(24)17(14(16)28)34-20-15(29)18(26-4)21(2,30)7-31-20/h8-20,25-30H,5-7,22-24H2,1-4H3 |
| InChI Key | VAVZWASKZVXMFU-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Melting Point | 119-123°C |
| Solubility | Soluble in Water |
Reference Reading
1. Mutational biosynthesis by idiotrophs of Micromonospora purpurea. I. Conversion of aminocyclitols to new aminoglycoside antibiotics
D Rosi, W A Goss, S J Daum J Antibiot (Tokyo). 1977 Jan;30(1):88-97. doi: 10.7164/antibiotics.30.88.
By mutation and strain improvement techniques idiotrophs of Micromonospora purpurea, the gentamicin-producing organism, were obtained which require an exogenous source of 2-deoxystreptamine in order to produce gentamicin. Streptamine incorporation afforded a mixture of 2-hydroxygentamicin C as a complex of essentially the C1 and C2 components whereas 2-deoxystreptamine when incorporated by the same idiotroph afforded the same mixture of C1, C2 and C1a gentamicins as the parent (m1) organism. The 2-hydroxygentamicin C complex exhibited broad-spectrum antibiotic activity with an in vitro potency less than that for the gentamicin C complex, but with greater activity against selected gentamicin C resistant organisms. The LD 50 (i.v.) in mice of the 2-hydroxygentamicin C complex indicated that it had approximately half the toxicity of the gentamicin C complex. 2, 5-Dideoxystreptamine affordeda C1, C2, and C1a mixture of 5-deoxygentamicins, which also had broad spectrum activity, and exhibited improved activity against several gentamicin-acetylating strains of resistant bacteria. The LD50 (i.v.) in mice of the 5-deoxygentamicin C complex indicated that it was about 2.5 times more toxic than the gentamicin C complex. Two derivatives of 2,5-dideoxystreptamine afforded the same mixture of 5-deoxygentamicins. 2-Epistreptamine upon supplementation to a broth containing growing cultures of these idiotrophs also produced antibiotic.
2. Mutational biosynthesis by idiotrophs of Micromonospora purpurea. II. Conversion of non-amino containing cyclitols to aminoglycoside antibiotics
S J Daum, D Rosi, W A Goss J Antibiot (Tokyo). 1977 Jan;30(1):98-105. doi: 10.7164/antibiotics.30.98.
A mutant of Micromonospora purpurea, which produces the gentamicin complex only when 2-deoxystreptamine is added to the fermentation medium, produces a new antibiotic complex, 2-hydroxygentamicin, when streptamine or 2,4,6/3,5-pentahydroxycyclohexanone is added to the fermentation medium. This mutant also produces the gentamicin complex when 2,4/3,5-tetrahydroxycyclohexanone is added to the fermentation medium. The C1 and C2 components of 2-hydroxygentamicin have broad spectrum in vitro antibacterial activity similar to the gentamicin C1 and C2 components, but with greater activity against some gentamicin-resistant strains.
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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 ╳
