Chloropolysporin B
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| Category | Antibiotics |
| Catalog number | BBF-00317 |
| CAS | 105650-11-1 |
| Molecular Weight | 1848.98 |
| Molecular Formula | C83H89Cl3N8O34 |
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Description
Chloropolysporin B is produced by the strain of Faenia interjecta SANK 60983. It has strong activity of anti-gram-positive bacteria, including clinically isolated methicillin-resistant Staphylococcus aureus (MRSA) and enterococcus bacteria. Chloropolysporin B and other glycopeptide antibiotics can also promote the growth of broiler chickens.
Specification
| Synonyms | 10,49-Dichloro-2D-O-de(3-amino-2,3,6-trideoxy-alpha-L-ribo-hexopyranosyl)avoparcin alpha |
| IUPAC Name | 2-(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy-5,15-dichloro-22-(3-chloro-4-hydroxyphenyl)-32,35,37-trihydroxy-19-[[2-(methylamino)-2-[4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyphenyl]acetyl]amino]-20,23,26,42,44-pentaoxo-18,48-bis[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]-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 | CC1C(C(CC(O1)OC2C3C(=O)NC(C4=C(C(=CC(=C4)O)O)C5=C(C=CC(=C5)C(C(=O)N3)NC(=O)C6C7=CC(=C(C(=C7)OC8=C(C=C(C=C8)C(C(C(=O)NC(C(=O)N6)C9=CC(=C(C=C9)O)Cl)NC(=O)C(C1=CC=C(C=C1)OC1C(C(C(C(O1)C)O)O)O)NC)OC1C(C(C(C(O1)CO)O)O)O)Cl)OC1C(C(C(C(O1)CO)O)O)O)OC1=C(C=C2C=C1)Cl)O)C(=O)O)N)O |
| InChI | InChI=1S/C83H89Cl3N8O34/c1-27-61(101)42(87)24-52(119-27)126-71-32-8-14-46(40(85)18-32)122-48-20-34-21-49(73(48)128-83-70(110)67(107)64(104)51(26-96)125-83)123-47-15-9-33(19-41(47)86)72(127-82-69(109)66(106)63(103)50(25-95)124-82)60(93-74(111)54(88-3)29-4-10-36(11-5-29)121-81-68(108)65(105)62(102)28(2)120-81)78(115)90-56(31-7-13-44(99)39(84)17-31)75(112)91-57(34)77(114)89-55-30-6-12-43(98)37(16-30)53-38(22-35(97)23-45(53)100)58(80(117)118)92-79(116)59(71)94-76(55)113/h4-23,27-28,42,50-52,54-72,81-83,88,95-110H,24-26,87H2,1-3H3,(H,89,114)(H,90,115)(H,91,112)(H,92,116)(H,93,111)(H,94,113)(H,117,118) |
| InChI Key | PCGBWZQZOMMXGB-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | gram-positive bacteria; fungi |
Reference Reading
1. Chloropolysporins A, B and C, novel glycopeptide antibiotics from Faenia interjecta sp. nov. V. Comparative studies of the biological properties
T Takatsu, T Katayama, M Nakajima, S Takahashi, T Haneishi, T Magaribuchi, M Tajima J Antibiot (Tokyo). 1987 Jul;40(7):946-52. doi: 10.7164/antibiotics.40.946.
Chloropolysporins A, B and C, as well as derivatives prepared from this group and alpha- and beta-avoparcins by enzymatic and mild acid hydrolysis, were active against Gram-positive bacteria including clinically isolated methicillin-resistant Staphylococci (MIC 0.39-6.25 micrograms/ml) and anaerobic enterobacteria (MIC 0.10-1.56 micrograms/ml). Derhamnosyl and demannosyl derivatives from both groups of antibiotics showed stronger activities than the parent compounds. The MIC and MBC values against Staphylococci were similar and were not effected by the presence of serum. Moreover, chloropolysporin C exhibited very strong synergistic effects with various beta-lactam antibiotics against methicillin-resistant strains of Staphylococcus aureus. Some of these compounds also protected mice from experimental infection with S. aureus. Acute toxicities of chloropolysporin by intravenous administration ranged from 215-290 mg/kg in mice. Chloropolysporin B as well as other glycopeptide antibiotics, showed distinctive growth promoting activity in broiler chickens.
2. Chloropolysporins A, B and C, novel glycopeptide antibiotics from Faenia interjecta sp. nov. IV. Partially deglycosylated derivatives
T Takatsu, S Takahashi, Y Takamatsu, T Shioiri, S Iwado, T Haneishi J Antibiot (Tokyo). 1987 Jul;40(7):941-5. doi: 10.7164/antibiotics.40.941.
Chloropolysporins A, B and C, new members of the glycopeptide antibiotic family, were enzymatically and chemically converted to their partially deglycosylated derivatives. The alpha- and beta-avoparcins were also deglycosylated by the same method. The conversions were achieved by treatments with rhamnosidase (Naringinase) and alpha-mannosidase, and by mild acid hydrolysis.
3. Chloropolysporins A, B and C, novel glycopeptide antibiotics from Faenia interjecta sp. nov. III. Structure elucidation of chloropolysporins
T Takatsu, S Takahashi, M Nakajima, T Haneishi, T Nakamura, H Kuwano, T Kinoshita J Antibiot (Tokyo). 1987 Jul;40(7):933-40. doi: 10.7164/antibiotics.40.933.
Structure elucidations of chloropolysporins A, B and C were achieved mainly by chemical degradation studies. These components possessed the same pseudoaglycone in common and their structures were closely related to that of beta-avoparcin. The structures of chloropolysporins differ from that of beta-avoparcin in the presence of vancomycinic acid moiety instead of monodechlorovancomycinic acid moiety and glucose, not ristosaminylglucose, in its side chain. Chloropolysporin C was identified as derhamnosylchloropolysporin B based on its 1H NMR and mass spectral analysis and degradation studies. Two minor components, chloropolysporins D and E, were identified as the epimers of each of chloropolysporins B and C, respectively, based on their Cotton effects and retention times on reverse phase HPLC.
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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 ╳
