Davercin

Cas：55224-05-0

Product Information：

Davercin, also known as Erythromycin Cyclocarbonate, is a bacteriostatic antibiotic macrolide produced by Streptomyces erythreus. It inhibits protein synthesis by binding to 50S ribosomal subunits. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins. Note: This product is supplied as ethanol solution (100mg/mL)

Chemical Formula: C38H65NO14

Exact Mass: 759.4405

Molecular Weight: 759.93

Elemental Analysis: C, 60.06; H, 8.62; N, 1.84; O, 29.47

Synonym: 

Erythromycin A

Erythromycin A 11,12-carbonate

Erythromycin A cyclic carbonate

Chemical Name: (3aR,4R,7R,8S,9S,10R,11R,13R,15R,15aR)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-11-hydroxy-8-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-3a,7,9,11,13,15-hexamethyldecahydro-6H-[1,3]dioxolo[4,5-c][1]oxacyclotetradecine-2,6,14(7H)-trione

InChi Key:

NKLGIWNNVDPGCA-ZDYKNUMJSA-N

InChi Code: InChI=1S/C38H65NO14/c1-14-25-38(10)32(52-35(44)53-38)20(4)27(40)18(2)16-36(8,45)31(51-34-28(41)24(39(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-37(9,46-13)30(42)23(7)48-26/h18-26,28-32,34,41-42,45H,14-17H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30+,31-,32-,34+,36-,37-,38-/m1/s1

Smiles Code:

CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]3O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@H]4OC(=O)O[C@]14C

Technical Data：

Appearance: Colorless solution (in ethanol, 100mg/mL)

Purity: >95% (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

In Vitro：

Erythromycin is used in treatment of respiratory, gastrointestinal, and genital tract infections, as well as skin and soft tissue infections. Erythromycin, with its ten chiral centers and two sugar substituents (L-cladinose and D-desosamine), is a good starting point for numerous medicinal chemistry efforts for improvement of its biological profile (better activity, higher stability, and improved bioavailability) since the first generation of macrolides, which had low toxicity and good tolerability, are unstable in acidic media, had low toxicity and good tolerability.

References：

1. Zhang W, Qiu L, Gong A, Yuan X. Isolation and characterization of a high-efficiency erythromycin A-degrading Ochrobactrum sp. strain. Mar Pollut Bull. 2017 Jan 30;114(2):896-902. doi: 10.1016/j.marpolbul.2016.10.076. PubMed PMID: 27863881.

2. Pierattini EC, Francini A, Raffaelli A, Sebastiani L. Morpho-physiological response of Populus alba to erythromycin: A timeline of the health status of the plant. Sci Total Environ. 2016 Nov 1;569-570:540-7. doi: 10.1016/j.scitotenv.2016.06.152. PubMed PMID: 27366984.

3. Chen D, Wu J, Liu W. [Biosynthesis-based production improvement and structure modification of erythromycin A]. Sheng Wu Gong Cheng Xue Bao. 2015 Jun;31(6):939-54. Review. Chinese. PubMed PMID: 26672369.

4. Jiang M, Fang L, Pfeifer BA. Improved heterologous erythromycin A production through expression plasmid re-design. Biotechnol Prog. 2013 Jul-Aug;29(4):862-9. doi: 10.1002/btpr.1759. PubMed PMID: 23804312.

5. Magee TV, Han S, McCurdy SP, Nguyen TT, Granskog K, Marr ES, Maguire BA, Huband MD, Chen JM, Subashi TA, Shanmugasundaram V. Novel 3-O-carbamoyl erythromycin A derivatives (carbamolides) with activity against resistant staphylococcal and streptococcal isolates. Bioorg Med Chem Lett. 2013 Mar 15;23(6):1727-31. doi: 10.1016/j.bmcl.2013.01.067. PubMed PMID: 23414806.

Products are for research use only. Not for human use.