Vancomycin EP Impurity A
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| Category | Antibiotics |
| Catalog number | BBF-03510 |
| CAS | 91700-98-0 |
| Molecular Weight | 1435.22 |
| Molecular Formula | C65H73Cl2N9O24 |
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Description
Vancomycin EP Impurity A is a glycopeptide antibiotic produced by Nocardia orientalis A51568.1. Activity against gram-positive bacteria.
Specification
| Synonyms | N2.1-demethylvancomycin B; N-Demethyl Vancomycin B; Norvancomycin; A51568 A |
| IUPAC Name | (1S,2R,18R,19R,22S,25R,28R,40S)-48-[(2S,3R,4S,5S,6R)-3-[(2S,4S,5S,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-19-[[(2R)-2-amino-3-methylpentanoyl]amino]-22-(2-amino-2-oxoethyl)-5,15-dichloro-2,18,32,35,37-pentahydroxy-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentazaoctacyclo[26.14.2.23,6.214,17.18,12.129,33.010,25.034,39]pentaconta-3,5,8(48),9,11,14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylic acid |
| Canonical SMILES | CCC(C)C(C(=O)NC1C(C2=CC(=C(C=C2)OC3=CC4=CC(=C3OC5C(C(C(C(O5)CO)O)O)OC6CC(C(C(O6)C)O)(C)N)OC7=C(C=C(C=C7)C(C8C(=O)NC(C9=C(C(=CC(=C9)O)O)C2=C(C=CC(=C2)C(C(=O)N8)NC(=O)C4NC(=O)C(NC1=O)CC(=O)N)O)C(=O)O)O)Cl)Cl)O)N |
| InChI | InChI=1S/C65H73Cl2N9O24/c1-5-22(2)44(69)58(88)75-48-50(82)25-7-10-36(31(66)13-25)96-38-15-27-16-39(54(38)100-64-55(53(85)52(84)40(21-77)98-64)99-42-20-65(4,70)56(86)23(3)95-42)97-37-11-8-26(14-32(37)67)51(83)49-62(92)74-47(63(93)94)30-17-28(78)18-35(80)43(30)29-12-24(6-9-34(29)79)45(59(89)76-49)73-60(90)46(27)72-57(87)33(19-41(68)81)71-61(48)91/h6-18,22-23,33,40,42,44-53,55-56,64,77-80,82-86H,5,19-21,69-70H2,1-4H3,(H2,68,81)(H,71,91)(H,72,87)(H,73,90)(H,74,92)(H,75,88)(H,76,89)(H,93,94)/t22?,23-,33-,40+,42-,44+,45+,46+,47-,48+,49-,50+,51+,52+,53-,55+,56+,64-,65-/m0/s1 |
| InChI Key | FGDOJVYPUSOORV-BKPBQXSSSA-N |
Properties
| Appearance | White to Off-White Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | >199°C (dec.) |
| Density | 1.67±0.1 g/cm3 |
Reference Reading
1. Solid-phase synthesis and antibacterial evaluations of N-demethylvancomycin derivatives
Nian-Huan Yao, Kit S Lam, Changqun Niu, James R Carlson, Gang Liu, Wen-Yi He Bioorg Med Chem Lett . 2005 May 2;15(9):2325-9. doi: 10.1016/j.bmcl.2005.02.086.
Twenty-five N-demethylvancomycin derivatives were synthesized on solid-support and their structures were determined by LC-MS/MS. Biological evaluation of these compounds indicated that bulky hydrophobic substituent on vancosamine of N-demethylvancomycin can increase antibacterial activity against vancomycin-resistant Enterococcus faecalis.
2. Affinity adsorbents for the vancomycin group of antibiotics
X Cheng, H Yan, J Yuan, B He, Q Zhao Biotechnol Appl Biochem . 2000 Feb;31(1):15-20. doi: 10.1042/ba19990039.
The vancomycin group of antibiotics kill Gram-positive bacteria by binding to nascent bacterial cell-wall peptidoglycan bearing the C-terminal sequence-D-Ala-D-Ala. In this paper, affinity adsorbents for the vancomycin group of antibiotics were prepared by immobilizing the peptidoglycan analogues -D-Ala-D-Ala, -succinyl-D-Ala and -succinyl-Gly on to crosslinked poly(N, N-dimethylacrylamide). The adsorption capacities of the three adsorbents for demethylvancomycin were 0.59, 0.35 and 0.29 mmol/g, respectively. The adsorption capacity of the adsorbent with-D-Ala-D-Ala for vancomycin was 0.53 mmol/g. In contrast, the adsorbent bearing -succinyl-L-Ala hardly adsorbed demethylvancomycin. Aqueous sodium carbonate (0.4 M)/acetonitrile (7/3, v/v) completely desorbed demethylvancomycin adsorbed on the adsorbents.
3. Antibiotic activities and affinities for bacterial cell wall analogue of N-demethylvancomycin and its derivatives
Z Song, X Cheng, H Yan, W Li, D Qi, B He J Antibiot (Tokyo) . 1998 Aug;51(8):750-6. doi: 10.7164/antibiotics.51.750.
N-Demethylvancomycin, which has been clinically used in China, is one member of vancomycin group (glycopeptide) antibiotics. It differs from vancomycin only in that methyl group on the amino group of the N-terminal residue of vancomycin has been replaced by H. By reductive alkylation of N-demethylvancomycin, we synthesized N-alkyl and N,N'-dialkyl N-demethylvancomycins, which closely correlated with vancomycin in structure. The association constants of the complexes of N-demethylvancomycin and its analogues with di-N-Ac-L-Lys-D-Ala-D-Ala and the antibiotic activity against Staphylococcus aureus of the glycopeptides were determined. Results showed that N-demethylvancomycin has higher affinity for bacterial cell wall analogue di-N-Ac-L-Lys-D-Ala-D-Ala and more potent antibiotic activity against Staphylococcus aureus than vancomycin. Both N-alkylation and N,N'-dialkylation of N-demethylvancomycin reduced the affinity and antibiotic activity. The longer the alkyl groups, the less potent antibiotic activities and lower affinities have the glycopeptides. The antibiotic activities against Staphylococcus aureus of N-demethylvancomycin and its analogues roughly parallel their affinities for di-N-Ac-L-Lys-D-Ala-D-Ala.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
