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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

Related Categories

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

Signal Word

Warning

Hazard Statements

H317

Hazard Classifications

Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, 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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