2-Hydroxygentamicin C2

2-Hydroxygentamicin C2

* Please be kindly noted products are not for therapeutic use. We do not sell to patients.

Category Antibiotics
Catalog number BBF-01000
CAS 60768-15-2
Molecular Weight 479.57
Molecular Formula C20H41N5O8

Online Inquiry

Description

2-Hydroxygentamicin C2 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-aminoethyl)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)N
InChI InChI=1S/C20H41N5O8/c1-7(21)9-5-4-8(22)18(31-9)32-15-10(23)12(26)11(24)16(13(15)27)33-19-14(28)17(25-3)20(2,29)6-30-19/h7-19,25-29H,4-6,21-24H2,1-3H3
InChI Key NOLNTDUUBSKKFZ-UHFFFAOYSA-N

Properties

Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria
Melting Point 115-119°C
Solubility Soluble in Water

Reference Reading

1. 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.
2. 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.

Recommended Products

Bio Calculators

Stock concentration: *
Desired final volume: *
Desired concentration: *

L

* 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
g/mol
g

Recently viewed products

Online Inquiry

Verification code
cartIcon
Inquiry Basket