Josamycin solution

Available from stock

Josamycin solution, 10 µg/ml in acetone

SKU
J0009

Category:

Synonyms
Kitasamycin A3 , Leucomycin A3 , Turimycin A5
16846-24-5
CAS-Number
C42H69NO15
Molecular Formula
827.99
Molecular Weight

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

Specifications

Purity
≥98% (UV)
Appearance
White to off-white powder
Identity
1H-NMR
Concentration
10 µg/ml in acetone

Properties

Solvents
water
Shipping
AMBIENT
Short Term Storage
+4°C
Long Term Storage
+4°C
Handling Advice
Protect from light and moisture.
Use / Stability
Stable for at least 2 years after receipt when stored at +4°C.
Hazard statements
H225, H319, H336
Precautionary statements
P210, P305 + P351 + P338, P370 + P378, P403 + P235
GHS Symbol
GHS02+GHS07
Signal word
Danger
Transportation
Packing Group II
Description
Josamycin is a member of the leucomycin family of macrolide antibiotics produced by Streptomyces kitasatoensis. It is an antimicrobial against a wide variety of pathogens. It has activity against Gram-positive an Gram-negative bacteria. The mechanism of action is via inhibition of bacterial protein biosynthesis by binding reversibly to the subunit 50S of the bacterial ribosome, inhibiting peptidyltransferase and ribosomal translocation, thereby inhibiting translocation of peptidyl tRNA. Josamycin may overcome anticancer drug resistance by inhibiting the binding of vinblastine or cyclosporin A to P-glycoprotein (Pgp). It is used to study the modification of phagocytosis and cytokine production by macrolide antibiotics and immunomodulatory effects.
Smiles
O=C1O[C@H](C)C/C=C/C=C/[C@H](O)[C@H](C)CC(CC=O)[C@H](O[C@@H]2O[C@H](C)[C@@H](O[C@@H]3O[C@@H](C)[C@H](OC(CC(C)C)=O)[C@](C)(O)C3)[C@@H](N(C)C)[C@H]2O)[C@@H](OC)[C@H](OC(C)=O)C1
InChi Key
XJSFLOJWULLJQS-LAEWXYAOSA-N
References
(1) K. Nitta, et al., J. Antibiot. 20, 181 (1967) , (2) T. Osono, et al., J. Antibiot. 20, 174 (1967) , (3) T. Bergan & B. Oydvin, Acta Pathol. Microbiol. Scand. B Microbiol. Immunol. 80, 101 (1972) , (4) E.L. Westerman, et al., Antimicrob. Agents Chemother. 9, 988 (1976) , (5) R.E. Reese, et al., Antimicrob. Agents Chemother. 10, 253 (1976) , (6) J.P. Guggenbichler, et al., Infection 21, 259 (1993) , (7) K. Morikawa, et al., Antimicrob. Agents Chemother. 38, 2643 (1994) , (8) T. Ono, et al., Chemotherapy 42, 159 (1996) , (9) L. Wang, et al., Clin. Exp. Pharmacol. Physiol. 27, 587 (2000) , (10) M. Lovmar, et al., J. Biol. Chem. 279, 53506 (2004) , (11) E.Y. Choi, et al., Biomed. Pharmacother. 105, 498 (2018)
InChi
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

Josamycin is a member of the leucomycin family of macrolide antibiotics produced by Streptomyces kitasatoensis. It is an antimicrobial against a wide variety of pathogens. It has activity against Gram-positive an Gram-negative bacteria. The mechanism of action is via inhibition of bacterial protein biosynthesis by binding reversibly to the subunit 50S of the bacterial ribosome, inhibiting peptidyltransferase and ribosomal translocation, thereby inhibiting translocation of peptidyl tRNA. Josamycin may overcome anticancer drug resistance by inhibiting the binding of vinblastine or cyclosporin A to P-glycoprotein (Pgp). It is used to study the modification of phagocytosis and cytokine production by macrolide antibiotics and immunomodulatory effects.

SKU: J0009 Category:

Additional information

Synonyms

Kitasamycin A3, Leucomycin A3, Turimycin A5
Purity

≥98% (UV)
Appearance

White to off-white powder
CAS-Number

16846-24-5
Molecular Formula

C42H69NO15
Molecular Weight

827.99
Identity

1H-NMR
Solvents

water
Smiles

O=C1O[C@H](C)C/C=C/C=C/[C@H](O)[C@H](C)CC(CC=O)[C@H](O[C@@H]2O[C@H](C)[C@@H](O[C@@H]3O[C@@H](C)[C@H](OC(CC(C)C)=O)[C@](C)(O)C3)[C@@H](N(C)C)[C@H]2O)[C@@H](OC)[C@H](OC(C)=O)C1
InChi Key

XJSFLOJWULLJQS-LAEWXYAOSA-N
Shipping

AMBIENT
Short Term Storage

+4°C
Long Term Storage

+4°C
Handling Advice

Protect from light and moisture.
Use / Stability

Stable for at least 2 years after receipt when stored at +4°C.
Hazard statements

H225, H319, H336
Precautionary statements

P210, P305 + P351 + P338, P370 + P378, P403 + P235
GHS Symbol

GHS02+GHS07
Signal word

Danger
Transportation

Packing Group II
References

(1) K. Nitta, et al., J. Antibiot. 20, 181 (1967), (2) T. Osono, et al., J. Antibiot. 20, 174 (1967), (3) T. Bergan & B. Oydvin, Acta Pathol. Microbiol. Scand. B Microbiol. Immunol. 80, 101 (1972), (4) E.L. Westerman, et al., Antimicrob. Agents Chemother. 9, 988 (1976), (5) R.E. Reese, et al., Antimicrob. Agents Chemother. 10, 253 (1976), (6) J.P. Guggenbichler, et al., Infection 21, 259 (1993), (7) K. Morikawa, et al., Antimicrob. Agents Chemother. 38, 2643 (1994), (8) T. Ono, et al., Chemotherapy 42, 159 (1996), (9) L. Wang, et al., Clin. Exp. Pharmacol. Physiol. 27, 587 (2000), (10) M. Lovmar, et al., J. Biol. Chem. 279, 53506 (2004), (11) E.Y. Choi, et al., Biomed. Pharmacother. 105, 498 (2018)
InChi

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
Quantity

1 ml, 5 ml, Bulk
cdx-Concentration

10 µg/ml in acetone

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