Kibdelin A
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| Category | Antibiotics |
| Catalog number | BBF-01538 |
| CAS | 103528-50-3 |
| Molecular Weight | 1775.38 |
| Molecular Formula | C81H84Cl4N8O29 |
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Description
Kibdelin A is originally isolated from Kibdelosporangium aridum subsp. largum SKF AAD-609. Kibdelin A is resistant to gram-positive bacteria and has similar effects against Staphylococcus aureus (including methicillin-resistant strains) as vancomycin.
Specification
| Synonyms | Ristomycin A aglycone, 5,22,31,55-tetrachloro-7-demethyl-64-O-demethyl-56-O-(2-deoxy-2-((1-oxodecyl)amino)-beta-D-glucopyranosyl)-42-O-alpha-D-mannopyranosyl-N15-methyl- |
| IUPAC Name | 5,15,32,65-tetrachloro-64-[6-(decanoylamino)-4,5-dihydroxy-3-(hydroxymethyl)oxan-2-yl]oxy-2,18,26,31,44,49-hexahydroxy-22-(methylamino)-21,35,38,54,56,59-hexaoxo-47-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7,13,28-trioxa-20,36,39,53,55,58-hexazaundecacyclo[38.14.2.23,6.214,17.219,34.18,12.123,27.129,33.141,45.010,37.046,51]hexahexaconta-3,5,8,10,12(64),14,16,23(61),24,26,29(60),30,32,41(57),42,44,46(51),47,49,62,65-henicosaene-52-carboxylic acid |
| Canonical SMILES | CCCCCCCCCC(=O)NC1C(C(C(C(O1)OC2=C3C=C4C=C2OC5=C(C=C(C=C5Cl)C(C6C(=O)NC(C7=C(C(=CC(=C7)O)OC8C(C(C(C(O8)CO)O)O)O)C9=C(C=CC(=C9)C(C(=O)N6)NC(=O)C4NC(=O)C1C2=C(C(=CC(=C2)OC2=C(C=CC(=C2)C(C(=O)NC(C(C2=CC(=C(O3)C=C2)Cl)O)C(=O)N1)NC)O)O)Cl)O)C(=O)O)O)Cl)CO)O)O |
| InChI | InChI=1S/C81H84Cl4N8O29/c1-3-4-5-6-7-8-9-10-53(100)87-78-68(106)65(103)40(28-94)80(122-78)121-71-50-22-33-23-51(71)118-70-42(83)19-34(20-43(70)84)64(102)62-77(113)91-60(79(114)115)38-24-35(96)25-49(119-81-69(107)67(105)66(104)52(29-95)120-81)54(38)37-17-30(11-14-44(37)97)57(73(109)93-62)88-74(110)58(33)89-75(111)59-39-26-36(27-46(99)55(39)85)116-48-21-31(12-15-45(48)98)56(86-2)72(108)92-61(76(112)90-59)63(101)32-13-16-47(117-50)41(82)18-32/h11-27,40,52,56-69,78,80-81,86,94-99,101-107H,3-10,28-29H2,1-2H3,(H,87,100)(H,88,110)(H,89,111)(H,90,112)(H,91,113)(H,92,108)(H,93,109)(H,114,115) |
| InChI Key | LBADJJYNXUZTCV-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; fungi |
Reference Reading
1. Kibdelins (AAD-609), novel glycopeptide antibiotics. II. Isolation, purification and structure
G Folena-Wasserman, B L Poehland, E W Yeung, D Staiger, L B Killmer, K Snader, J J Dingerdissen, P W Jeffs J Antibiot (Tokyo). 1986 Oct;39(10):1395-406. doi: 10.7164/antibiotics.39.1395.
A new glycopeptide antibiotic complex was isolated from the fermentation culture of Kibdelosporangium aridum subsp. largum (SK&F AAD-609) by affinity chromatography on a D-alanyl-D-alanine agarose column. This major components of the complex were resolved by preparative reversed-phase HPLC. Mild acid hydrolysis showed that the new antibiotics have the same mannosyl aglycon (2) as the aridicins. FAB mass spectrometry, isoelectric focusing, potentiometric titration and carbohydrate and fatty acid analyses were used to determine the structures of the five major components of the complex. These studies showed that the kibdelins differ from the aridicins only in the oxidation level at the C-6 position of the amino sugar. Kibdelin A (5), B (6), C1 (7), C2 (8) and D (9) are a series of N-acylglucosamine analogs containing saturated straight and branched chain C10-C12 fatty acids whereas, in kibdelin D the fatty acid component is (Z)-4-decenoic acid.
2. Kibdelins, novel glycopeptide antibiotics. I. Discovery, production, and biological evaluation
M C Shearer, A J Giovenella, S F Grappel, R D Hedde, R J Mehta, Y K Oh, C H Pan, D H Pitkin, L J Nisbet J Antibiot (Tokyo). 1986 Oct;39(10):1386-94. doi: 10.7164/antibiotics.39.1386.
A new subspecies of Kibdelosporangium aridum subsp. largum (SK&F AAD-609), was isolated and shown to produce novel glycopeptides related to aridicins, but containing a homologous series of glycolipids based on N-acylglucosamine. These compounds showed improvements over the aridicins in in vitro activity and were effective in mouse protection studies against a range of Gram-positive bacteria, including methicillin resistant staphylococci. Pharmacokinetic studies indicated that they have high serum concentrations and long-acting potential. The kibdelin complex modified rumen metabolism in a manner favorable for growth promotion.
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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 ╳
