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48760

Sigma-Aldrich

Gentamicin sulfate from Micromonospora purpurea

≥590 μg/mg of gentamicin

Synonym(s):

Gentamicin C1

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About This Item

Linear Formula:
C19-21H39-43N5O7 · 2.5H2SO4
CAS Number:
1405-41-0
EC Number:
215-778-9
MDL number:
MFCD00270181
UNSPSC Code:
51281651
eCl@ss:
42020823
PubChem Substance ID:
329757401
NACRES:
NA.76

biological source

Micromonospora purpurea

Quality Level

200

form

powder

optical activity

[α]/D 107.0 to 121.0°, c = 10% in H2O

specific activity

≥590 μg/mg of gentamicin

mol wt

Mr 694-723

loss

≤18.0% loss on drying

color

white to off-white

pH

3.5-5.5 (4% in H2O)

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
mycoplasma

mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

OS(O)(=O)=O.CN[C@@H]1[C@@H](O)[C@H](OC[C@]1(C)O)O[C@H]2[C@H](N)C[C@H](N)[C@@H](O[C@H]3O[C@H](CN)CC[C@H]3N)[C@@H]2O.CN[C@@H]4[C@@H](O)[C@H](OC[C@]4(C)O)O[C@H]5[C@H](N)C[C@H](N)[C@@H](O[C@H]6O[C@@H](CC[C@H]6N)[C@@H](C)N)[C@@H]5O.CN[C@H](C)[C@@H]7CC[C@@H](N)[C@H](O7)O[C@@H]8[C@@H](N)C[C@@H](N)[C@H](O[C@H]9OC[C@](C)(O)[C@H](NC)[C@H]9O)[C@H]8O

InChI

1S/C21H43N5O7.C20H41N5O7.C19H39N5O7.H2O4S/c1-9(25-3)13-6-5-10(22)19(31-13)32-16-11(23)7-12(24)17(14(16)27)33-20-15(28)18(26-4)21(2,29)8-30-20;1-8(21)12-5-4-9(22)18(30-12)31-15-10(23)6-11(24)16(13(15)26)32-19-14(27)17(25-3)20(2,28)7-29-19;1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17;1-5(2,3)4/h9-20,25-29H,5-8,22-24H2,1-4H3;8-19,25-28H,4-7,21-24H2,1-3H3;8-18,24-27H,3-7,20-23H2,1-2H3;(H2,1,2,3,4)/t9-,10-,11+,12-,13+,14+,15-,16-,17+,18-,19-,20-,21+;8-,9-,10+,11-,12+,13+,14-,15-,16+,17-,18-,19-,20+;8-,9+,10-,11+,12-,13+,14+,15-,16+,17+,18+,19-;/m110./s1

InChI key

RDEIXVOBVLKYNT-HDZPSJEVSA-N

General description

Chemical structure: aminoglycoside

Application

Used as a selection agent (gentamicin-resistance gene) in molecular biology applications. It inhibits the growth of a wide variety of grampositive and gram-negative microorganisms including strains resistant to tetracycline, chloramphenicol, kanamycin and colistin, particularly strains of Pseudomonas, Proteus, Staphylococcus and Streptococcus.

Biochem/physiol Actions

Mode of Action: Inhibits protein synthesis by binding to L6 protein of 50S ribosomal subunit.
Antimicrobial spectrum: Gram-negative and Gram-positive bacteria, and mycoplasma.

Packaging

1g, 5g, 25g

Unit Definition

1 U corresponds to 1 μg of the USP gentamicin sulfate reference standard

Preparation Note

Freely soluble in water, practically insoluble in alcohol and ether.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H317

Hazard Classifications

Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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