Cladinose | CAS# 470-12-2 | antibiotic

MedKoo Cat#: 413047 | Name: Cladinose

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cladinose is a hexose deoxy sugar that in several antibiotics is attached to the macrolide ring. In ketolides, a relatively new class of antibiotics, the cladinose is replaced with a keto group.

Chemical Structure

Cladinose

CAS#470-12-2

Theoretical Analysis

MedKoo Cat#: 413047

Name: Cladinose

CAS#: 470-12-2

Chemical Formula: C8H16O4

Exact Mass: 176.1049

Molecular Weight: 176.21

Elemental Analysis: C, 54.53; H, 9.15; O, 36.32

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Cladinose

IUPAC/Chemical Name

2,6-Dideoxy-3-C-methyl-3-O-methyl-ribo-hexose

InChi Key

AJSDVNKVGFVAQU-PRJMDXOYSA-N

InChi Code

InChI=1S/C8H16O4/c1-6(10)7(11)8(2,12-3)4-5-9/h5-7,10-11H,4H2,1-3H3/t6-,7-,8+/m1/s1

SMILES Code

O=CC[C@]([C@@H]([C@@H](C)O)O)(C)OC

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 176.21 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Ajito K, Kurihara K, Shibahara S, Hara O, Shimizu A, Araake M, Omoto S. Cladinose analogues of sixteen-membered macrolide antibiotics. II. Preparation of pharmacokinetically improved analogues via biotransformation. J Antibiot (Tokyo). 1997 Jan;50(1):92-5. PMID: 9066773. 2: Randolph JT, Waid P, Nichols C, Sauer D, Haviv F, Diaz G, Bammert G, Besecke LM, Segreti JA, Mohning KM, Bush EN, Wegner CD, Greer J. Nonpeptide luteinizing hormone-releasing hormone antagonists derived from erythromycin A: design, synthesis, and biological activity of cladinose replacement analogues. J Med Chem. 2004 Feb 26;47(5):1085-97. doi: 10.1021/jm030418i. PMID: 14971889. 3: Abdelghaffar H, Vazifeh D, Labro MT. Erythromycin A-derived macrolides modify the functional activities of human neutrophils by altering the phospholipase D-phosphatidate phosphohydrolase transduction pathway: L-cladinose is involved both in alterations of neutrophil functions and modulation of this transductional pathway. J Immunol. 1997 Oct 15;159(8):3995-4005. PMID: 9378989. 4: Fernandes P, Martens E, Pereira D. Nature nurtures the design of new semi- synthetic macrolide antibiotics. J Antibiot (Tokyo). 2017 May;70(5):527-533. doi: 10.1038/ja.2016.137. Epub 2016 Nov 30. PMID: 27899792; PMCID: PMC5509991. 5: Ren J, Deng L, Niu D, Wang Z, Fan B, Li Z, Zhang J, Li C. Isolation and identification of a novel erythromycin-degrading fungus, Curvularia sp. RJJ-5, and its degradation pathway. FEMS Microbiol Lett. 2020 Dec 18:fnaa215. doi: 10.1093/femsle/fnaa215. Epub ahead of print. PMID: 33338238. 6: Kwiatkowska B, Maślińska M. Macrolide therapy in chronic inflammatory diseases. Mediators Inflamm. 2012;2012:636157. doi: 10.1155/2012/636157. Epub 2012 Aug 21. PMID: 22969171; PMCID: PMC3432395. 7: Zhu ZJ, Krasnykh O, Pan D, Petukhova V, Yu G, Liu Y, Liu H, Hong S, Wang Y, Wan B, Liang W, Franzblau SG. Structure-activity relationships of macrolides against Mycobacterium tuberculosis. Tuberculosis (Edinb). 2008 Aug;88 Suppl 1:S49-63. doi: 10.1016/S1472-9792(08)70036-2. PMID: 18762153. 8: CORCORAN JW. Actinomycete antibiotics. II. Participation of the methionine methyl group in the biogenesis of L-cladinose, a branched chain monosaccharide. J Biol Chem. 1961 Jun;236:PC27-8. PMID: 13695466. 9: Lazarevski T, Tamburasev Z, Djokić S. Erythromycin series. V. Quantitative analysis of cladinose and methylcladinoside by densitometry of thin-layer chromatograms. J Chromatogr. 1977 Feb 11;132(2):309-13. doi: 10.1016/s0021-9673(00)89305-x. PMID: 833239. 10: Georgopapadakou NH. The wobbly status of ketolides: where do we stand? Expert Opin Investig Drugs. 2014 Oct;23(10):1313-9. doi: 10.1517/13543784.2014.954036. Epub 2014 Aug 25. PMID: 25154307.