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59983

Sigma-Aldrich

Josamycin

≥90% (HPLC)

Synonym(s):

Leucomycin A3

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About This Item

Empirical Formula (Hill Notation):
C42H69NO15
CAS Number:
Molecular Weight:
827.99
EC Number:
MDL number:
UNSPSC Code:
51102829
PubChem Substance ID:
NACRES:
NA.85

Quality Level

Assay

≥90% (HPLC)

form

powder

color

white to slightly yellow

antibiotic activity spectrum

Gram-positive bacteria

Mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

CO[C@H]1[C@@H](CC(=O)O[C@H](C)C\C=C\C=C\[C@H](O)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@@H]2O[C@H](C)[C@@H](O[C@H]3C[C@@](C)(O)[C@@H](OC(=O)CC(C)C)[C@H](C)O3)[C@@H]([C@H]2O)N(C)C)OC(C)=O

InChI

1S/C42H69NO15/c1-23(2)19-32(47)56-40-27(6)53-34(22-42(40,8)50)57-37-26(5)54-41(36(49)35(37)43(9)10)58-38-29(17-18-44)20-24(3)30(46)16-14-12-13-15-25(4)52-33(48)21-31(39(38)51-11)55-28(7)45/h12-14,16,18,23-27,29-31,34-41,46,49-50H,15,17,19-22H2,1-11H3/b13-12+,16-14+/t24-,25-,26-,27+,29+,30+,31-,34+,35-,36-,37-,38+,39+,40+,41+,42-/m1/s1

InChI key

XJSFLOJWULLJQS-NGVXBBESSA-N

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General description

Chemical structure: macrolide

Application

Josamycin is used to study the modification of phagocytosis and cytokine production by macrolide antibiotics, immunomodulatory effects, the suppression of matrix metalloproteinase production as well as study bacteria protein synthesis at the level of the the 23S rRNA, 50S ribosomal subunit.

Biochem/physiol Actions

Josamycin inhibits bacterial protein biosynthesis by inhibiting peptidyltransferase and ribosomal translocation, and depleting the intracellular pools of aminoacyl-tRNAs available for protein synthesis by drop-off and incomplete peptidyl-tRNA hydrolase activity. It slows down formation of the first peptide bond of a nascent peptide in an amino acid-dependent way and inhibits formation of the second or third peptide bond.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

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

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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Immunomodulatory effects of three macrolides, midecamycin acetate, josamycin, and clarithromycin, on human T-lymphocyte function in vitro.
K Morikawa, F Oseko, et al.
Antimicrobial Agents and Chemotherapy, 38, 2634-2647 (1994)
K Kanai et al.
The European respiratory journal, 23(5), 671-678 (2004-06-05)
It is well known that low-dose and long-term administration of macrolide antibiotics favourably modify the clinical status of chronic airway inflammatory diseases. However, the therapeutic mode of action of macrolide antibiotics is not well understood. The present study aimed to
Elena Ortega et al.
The Journal of antimicrobial chemotherapy, 53(2), 367-370 (2004-01-20)
The aim of this study was to determine whether pre-incubation of peritoneal or splenic cells with different doses of the macrolides erythromycin A (14-membered ring), azithromycin (15-membered ring) and josamycin (16-membered ring) affects their phagocytic activity or cytokine production. Peritoneal
Xue-Mei Ou et al.
Respirology (Carlton, Vic.), 13(1), 63-72 (2008-01-17)
To examine the effect of a 14-membered ring macrolide on airway mucus hypersecretion in rats treated with LPS. Mucus hypersecretion in rat airways was induced by intratracheal instillation of LPS. Rats treated with or without LPS were administered roxithromycin (1-10
Susan Boyle-Vavra et al.
Antimicrobial agents and chemotherapy, 47(3), 1028-1036 (2003-02-27)
We found an increased abundance of pbpB-specific transcripts in vancomycin intermediate-resistant Staphylococcus aureus (VISA) isolates compared with that found in paired, genetically identical, susceptible isolates. This difference in expression cannot be explained by differences in the pbpB promoter sequence. Since

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