5-Deoxygentamicin C1

5-Deoxygentamicin C1

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Category Antibiotics
Catalog number BBF-01347
CAS 60768-21-0
Molecular Weight 477.59
Molecular Formula C21H43N5O7

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Description

It is produced by the strain of Micromonospora purpurea Vib. The compound has anti-gram-positive and anti-gram-negative activities.

Specification

Synonyms 5-Deoxygentamicin C(sub 1); 2,4-Diamino-5-{[3-deoxy-4-C-methyl-3-(methylamino)pentopyranosyl]oxy}-3-hydroxycyclohexyl 2-amino-2,3,4,6,7-pentadeoxy-6-(methylamino)heptopyranoside
IUPAC Name 2-[2,4-diamino-5-[3-amino-6-[1-(methylamino)ethyl]oxan-2-yl]oxy-3-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol
Canonical SMILES CC(C1CCC(C(O1)OC2CC(C(C(C2N)O)N)OC3C(C(C(CO3)(C)O)NC)O)N)NC
InChI InChI=1S/C21H43N5O7/c1-9(25-3)11-6-5-10(22)19(31-11)32-12-7-13(15(24)16(27)14(12)23)33-20-17(28)18(26-4)21(2,29)8-30-20/h9-20,25-29H,5-8,22-24H2,1-4H3
InChI Key XKXZNTULXUJLSZ-UHFFFAOYSA-N

Properties

Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria

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.

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* 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

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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