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H5527

Sigma-Aldrich

Hygromycin B solution from Streptomyces hygroscopicus

≥60% (HPLC), 45-60 mg/mL in H2O, γ-irradiated

Synonym(s):

Hygromycin b, Hygrovetine

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About This Item

Empirical Formula (Hill Notation):
C20H37N3O13
CAS Number:
31282-04-9
Molecular Weight:
527.52
Beilstein:
6755837
MDL number:
MFCD06795479
UNSPSC Code:
51102829
PubChem Substance ID:
24895698
NACRES:
NA.85

biological source

Streptomyces hygroscopicus

Quality Level

200

sterility

γ-irradiated

concentration

≥60% (HPLC)
45-60 mg/mL in H2O

color

yellow-brown to orange

antibiotic activity spectrum

viruses

Mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

CN[C@H]1C[C@@H](N)[C@H](O)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@@H]3OC4(O[C@H]([C@H](N)CO)[C@H](O)[C@H](O)[C@H]4O)O[C@H]23)[C@@H]1O

InChI

1S/C20H37N3O13/c1-23-7-2-5(21)9(26)15(10(7)27)33-19-17-16(11(28)8(4-25)32-19)35-20(36-17)18(31)13(30)12(29)14(34-20)6(22)3-24/h5-19,23-31H,2-4,21-22H2,1H3/t5-,6-,7+,8-,9+,10-,11+,12-,13+,14-,15-,16+,17+,18-,19+,20+/m1/s1

InChI key

GRRNUXAQVGOGFE-XKIAHZFYSA-N

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General description

Chemical structure: aminoglycoside

Application

Hygromycin B is an aminoglycoside antibiotic isolated from Streptomyces hygroscopicus. It has been used to study protein synthesis at the level of the 70S ribosome translocation and mRNA template misreading, as an antiviral agent by selectively penetrating cells rendered permeable by virus infection and inhibiting translation, and as a selection agent for hygromycin resistance gene transformed cells. It is recommended for use as a selection agent at 100-800 μg/mL, specifically at 100 μg/mL for prokaryotes, 200 μg/mL for lower eukaryotes and 150-400 μg/mL for higher eukaryotes.

Biochem/physiol Actions

Mode of action: The product acts by inhibiting protein synthesis by inducing the misreading of the m-RNA template in the prokaryote, with the potency to inhibit translation.

Antimicrobial Spectrum: Hygromycin B acts against bacteria, fungi and higher eukaryotic cells.

Caution

Hygromycin B products should be stored as supplied at 2-8°C, and the dry solid is stable for at least 5 years if stored at 2-8°C. It is stable at 37°C for 30 days.

Preparation Note

This product is a solution that is =60% (HPAE), 45-60 mg/mL in H2O, and γ-irradiated .

Signal Word

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 3 Dermal - Acute Tox. 3 Oral - Eye Dam. 1 - Resp. Sens. 1

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

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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Iksung Jin et al.
Proceedings of the National Academy of Sciences of the United States of America, 109(23), 9131-9136 (2012-05-24)
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The Journal of organic chemistry, 77(13), 5801-5807 (2012-06-06)
Concise and efficient syntheses of the aminocyclitol cores of hygromycin A (HMA) and methoxyhygromycin (MHM) have been achieved starting from readily available myo-inositol. Reductive cleavage of myo-inositol orthoformate to the corresponding 1,3-acetal, stereospecific introduction of the amino group via the
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BMC microbiology, 12, 204-204 (2012-09-13)
The genus Mycobacterium (M.) comprises highly pathogenic bacteria such as M. tuberculosis as well as environmental opportunistic bacteria called non-tuberculous mycobacteria (NTM). While the incidence of tuberculosis is declining in the developed world, infection rates by NTM are increasing. NTM
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Organic letters, 14(23), 5896-5899 (2012-11-15)
A chiral pool based synthetic strategy that leads from the readily available and inexpensive C(2)-symmetric tartaric acids to the chiral O-isopropylidenebenzooxazole--a convenient precursor to the aminocyclitol core of hygromycin A as well as the chiral γ-disilyloxybutyrolactone--a pivotal intermediate to approach
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The increasing interest in renewable energy has attracted more research attention on biofuels. In order to generate sustainable amount of biomass feedstock from dedicated biofuel crops such as switchgrass they need to be genetically improved. Genetic transformation is one of
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