A-82548A
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| Category | Antibiotics |
| Catalog number | BBF-03171 |
| CAS | 171423-45-3 |
| Molecular Weight | 884.14 |
| Molecular Formula | C47H81NO14 |
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Description
A82548A is a macrolide antibiotic containing spiroacetal produced by Streptomyces diastatochromogenes.
Specification
| Synonyms | A82548A |
| IUPAC Name | (1S,3S,6S,6'R,8S,9E,14S,15R,16R,17R,18R,19S,20R,21E,25S,27R,29R)-16-[(2S,4S,5S,6S)-5-(dimethylamino)-4-hydroxy-6-methyloxan-2-yl]oxy-5,15,17,19,20-pentahydroxy-6'-[(2R)-2-hydroxybutyl]-6,14,18,20,29-pentamethylspiro[4,24,28-trioxatricyclo[23.3.1.03,8]nonacosa-9,21-diene-27,2'-oxane]-23-one |
| Canonical SMILES | CCC(CC1CCCC2(O1)CC3C(C(O2)CC4C(CC(C(O4)O)C)C=CCCCC(C(C(C(C(C(C(C=CC(=O)O3)(C)O)O)C)O)OC5CC(C(C(O5)C)N(C)C)O)O)C)C)O |
| InChI | InChI=1S/C47H81NO14/c1-10-32(49)22-33-17-14-19-47(61-33)25-37-28(4)35(62-47)24-36-31(21-27(3)45(55)59-36)16-13-11-12-15-26(2)41(52)43(60-39-23-34(50)40(48(8)9)30(6)57-39)42(53)29(5)44(54)46(7,56)20-18-38(51)58-37/h13,16,18,20,26-37,39-45,49-50,52-56H,10-12,14-15,17,19,21-25H2,1-9H3/b16-13+,20-18+/t26-,27-,28+,29+,30-,31+,32+,33+,34-,35-,36-,37-,39-,40+,41+,42+,43+,44-,45?,46+,47+/m0/s1 |
| InChI Key | LFLPRACEAAMLQA-BYILSSOKSA-N |
Properties
| Appearance | Crystal |
| Melting Point | 118-120°C |
Reference Reading
1. Yokonolide B, a novel inhibitor of auxin action, blocks degradation of AUX/IAA factors
Ken-ichiro Hayashi, Alan M Jones, Kentaro Ogino, Atsushi Yamazoe, Yutaka Oono, Masahiko Inoguchi, Hirokiyo Kondo, Hiroshi Nozaki J Biol Chem. 2003 Jun 27;278(26):23797-806. doi: 10.1074/jbc.M300299200. Epub 2003 Apr 9.
Yokonolide B (YkB; also known as A82548A), a spiroketal-macrolide, was isolated from Streptomyces diastatochromogenes B59 in a screen for inhibitors of beta-glucoronidase expression under the control of an auxin-responsive promoter in Arabidopsis. YkB inhibits the expression of auxin-inducible genes as shown using native and synthetic auxin promoters as well as using expression profiling of 8300 Arabidopsis gene probes but does not affect expression of an abscisic acid- and a gibberellin A3-inducible gene. The mechanism of action of YkB is to block AUX/IAA protein degradation; however, YkB is not a general proteasome inhibitor. YkB blocks auxin-dependent cell division and auxin-regulated epinastic growth mediated by auxin-binding protein 1. Gain of function mutants such as shy2-2, slr1, and axr2-1 encoding AUX/IAA transcriptional repressors and loss of function mutants encoding components of the ubiquitin-proteolytic pathway such as axr1-3 and tir1-1, which display increased AUX/IAAs protein stability, are less sensitive to YkB, although axr1 and tir1 mutants were sensitive to MG132, a general proteasome inhibitor, consistent with a site of action downstream of AXR1 and TIR. YkB-treated seedlings displayed similar phenotypes as dominant AUX/IAA mutants. Taken together, these results indicate that YkB acts to block AUX/IAA protein degradation upstream of AXR and TIR, links a shared element upstream of AUX/IAA protein stability to auxin-induced cell division/elongation and to auxin-binding protein 1, and provides a new tool to dissect auxin signal transduction.
2. Structure of the new spiroketal-macrolide A82548A
H A Kirst, S H Larsen, J W Paschal, J L Occolowitz, L C Creemer, J L Steiner, E Lobkovsky, J Clardy J Antibiot (Tokyo). 1995 Sep;48(9):990-6. doi: 10.7164/antibiotics.48.990.
A new member of the spiroketal-containing macrolide class of fermentation-derived natural products was isolated from mycelial extracts of Streptomyces diastatochromogenes. The principal component, A82548A, was shown to possess a 22-membered macrolide ring system onto which was incorporated both a spiroketal and a hemiketal moiety. Relative stereochemistry was established by single crystal X-ray diffraction studies. Absolute stereochemistry was determined via hydrolysis of the amino sugar glycosidically linked to the aglycone, which was identified as L-kedarosamine. The overall three-dimensional structure is closely related to that of the macrolides cytovaricin, rutamycin, and ossamycin.
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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 ╳
