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L6004

Sigma-Aldrich

Lincomycin hydrochloride

≥90% (TLC)

Synonym(s):

Epilincomycin, Lincomycin HCL, Lincocin hydrochloride, Methyl 6,8-dideoxy-6-(1-methyl-4-propyl-2-pyrrolidinecarboxamido)-1-thio-D-erythro-α-D-galactooctopyranoside hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C18H34N2O6S · HCl
CAS Number:
859-18-7
Molecular Weight:
443.00
Beilstein:
4171650
EC Number:
212-726-7
MDL number:
MFCD00083647
UNSPSC Code:
51284507
PubChem Substance ID:
329817633
NACRES:
NA.85

Assay

≥90% (TLC)

potency

800-900 units per mg

color

white to faint yellow

solubility

H2O: soluble 50 mg/mL

antibiotic activity spectrum

Gram-positive bacteria

Mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

Cl.CCC[C@@H]1C[C@H](N(C)C1)C(=O)N[C@H]([C@@H](C)O)[C@H]2O[C@H](SC)[C@H](O)[C@@H](O)[C@H]2O

InChI

1S/C18H34N2O6S.ClH/c1-5-6-10-7-11(20(3)8-10)17(25)19-12(9(2)21)16-14(23)13(22)15(24)18(26-16)27-4;/h9-16,18,21-24H,5-8H2,1-4H3,(H,19,25);1H/t9-,10-,11+,12-,13+,14-,15-,16-,18-;/m1./s1

InChI key

POUMFISTNHIPTI-BOMBIWCESA-N

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General description

Chemical structure: macrolide

Application

Lincomycin hydrochloride is an antibiotic used to study the inhibition of protein synthesis, bacterial antibiotic resistance, and protein and surfactant binding It is produced by Streptomyces lincolnensis var. lincolnensis.

Biochem/physiol Actions

Mode of action: Lincomycin inhibits bacterial protein synthesis by forming cross-links within the peptidyl transferase loop region of the 23S rRNA.†

Antimicrobial spectrum: Lincomycin hydrochloride is effective against gram-positive bacteria.

Preparation Note

This product is soluble in water at 50 mg/mL, yielding a clear, colorless solution.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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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H Malke et al.
Antimicrobial agents and chemotherapy, 19(1), 91-100 (1981-01-01)
The phenomenon of zonal resistance to lincomycin, which is characteristic of most clinical isolates with lincomycin resistance in Streptococcus pyogenes, has been studied. These strains grow within a defined concentration range of lincomycin (approximately 60 to 200 microgram/ml), or at
Charlotte M M Gommers et al.
Plant physiology, 185(1), 67-76 (2021-02-26)
When germinating in the light, Arabidopsis (Arabidopsis thaliana) seedlings undergo photomorphogenic development, characterized by short hypocotyls, greening, and expanded cotyledons. Stressed chloroplasts emit retrograde signals to the nucleus that induce developmental responses and repress photomorphogenesis. The nuclear targets of these
Neelam Keswani et al.
Journal of biochemistry, 148(1), 71-84 (2010-04-02)
The thermodynamics of interaction of neomycin and lincomycin with bovine serum albumin (BSA) and human serum albumin (HSA) has been studied using isothermal titration calorimetry (ITC), in combination with UV-visible, steady state and time resolved fluorescence spectroscopic measurements. Neomycin is
Phillip A Davis et al.
Photosynthesis research, 112(3), 153-161 (2012-06-15)
Plants use light to fix carbon through the process of photosynthesis but light also causes photoinhibition, by damaging photosystem II (PSII). Plants can usually adjust their rate of PSII repair to equal the rate of damage, but under stress conditions
Kazunori Miyata et al.
Photosynthesis research, 113(1-3), 165-180 (2012-07-17)
When visible light is excess, the photosynthetic machinery is photoinhibited. The extent of net photoinhibition of photosystem II (PSII) is determined by a balance between the rate of photodamage to D1 and some other PSII proteins and the rate of
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