Papulacandin A
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| Category | Antibiotics |
| Catalog number | BBF-02358 |
| CAS | 61036-46-2 |
| Molecular Weight | 887.02 |
| Molecular Formula | C47H66O16 |
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Description
It is produced by the strain of Papularia sphaerosperma. It has strong anti-yeast effect, but no effect on filiform fungi, bacteria and protozoa. It has no cross-resistance with polyene antibiotics, Conocandin and azole antifungal chemotherapy drugs, but has partial cross-resistance with Echinocandin B. Among the four components, Papulacandin C has the strongest activity and Papulacandin D has the weakest activity.
Specification
| Synonyms | 1,1-O-(4,6-Dihydroxy-1,2-phenylenemethylene)-4-O-[6-O-(1-oxo-2,4-decadienyl)-β-D-galactopyranosyl]-α-D-glucopyranose3-(7-hydroxy-8,14-dimethylhexadeca-2,4,8,10-tetraenoate); β-D-Galactopyranoside, (1S,3'R,4'R,5'R,6'R)-3',4',5',6'-tetrahydro-3',5,7-trihydroxy-4'-[(7-hydroxy-8,14-dimethyl-1-oxo-2,4,8,10-hexadecatetraenyl)oxy]-6'-(hydroxymethyl)spiro[isobenzofuran-1(3H),2'-[2H]pyran]-5'-yl,6-(2,4-decadienoate) |
| IUPAC Name | [(3S,3'R,4'R,5'R,6'R)-5'-[(2S,3R,4S,5R,6R)-6-[[(2E,4E)-deca-2,4-dienoyl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-3',4,6-trihydroxy-6'-(hydroxymethyl)spiro[1H-2-benzofuran-3,2'-oxane]-4'-yl] (2E,4E,7S,8E,10E,14S)-7-hydroxy-8,14-dimethylhexadeca-2,4,8,10-tetraenoate |
| Canonical SMILES | CCCCCC=CC=CC(=O)OCC1C(C(C(C(O1)OC2C(OC3(C(C2OC(=O)C=CC=CCC(C(=CC=CCCC(C)CC)C)O)O)C4=C(CO3)C=C(C=C4O)O)CO)O)O)O |
| InChI | InChI=1S/C47H66O16/c1-5-7-8-9-10-11-17-22-37(52)58-28-36-40(54)41(55)42(56)46(60-36)62-43-35(26-48)63-47(39-31(27-59-47)24-32(49)25-34(39)51)45(57)44(43)61-38(53)23-18-13-16-21-33(50)30(4)20-15-12-14-19-29(3)6-2/h10-13,15-18,20,22-25,29,33,35-36,40-46,48-51,54-57H,5-9,14,19,21,26-28H2,1-4H3/b11-10+,15-12+,16-13+,22-17+,23-18+,30-20+/t29-,33-,35+,36+,40-,41-,42+,43+,44-,45+,46-,47-/m0/s1 |
| InChI Key | DPVWBQZOSHCQTG-NVTMJBNDSA-N |
Properties
| Appearance | Colorless Amorphous Powder |
| Antibiotic Activity Spectrum | Yeast |
| Boiling Point | 1038.4°C at 760 mmHg |
| Melting Point | 171-173°C |
| Density | 1.32 g/cm3 |
| Solubility | Soluble in Chloroform, Methanol, Ethanol, DMF, Acetone, Ethyl Acetate |
Reference Reading
1. Synthesis and antifungal properties of papulacandin derivatives
Marjolein van der Kaaden, Eefjan Breukink, Roland J Pieters Beilstein J Org Chem. 2012;8:732-7. doi: 10.3762/bjoc.8.82. Epub 2012 May 14.
Derivatives of an antifungal agent that targets the β-(1,3)-D-glucan synthase, papulacandin D, were synthesized and tested for activity. The papulacandin D structure contains a challenging benzannulated spiroketal unit, which is introduced in a palladium-catalyzed cross-coupling reaction of a glycal silanolate and an aryl iodide followed by an oxidative spiroketalization. Four different variants were made, differing in the nature of the acyl side chain with respect to the length, and in the number and stereochemistry of the double bonds. Moderate biological activity was observed for the derivatives with a side chain based on palmitic acid and linoleic acid.
2. Pestiocandin, a new papulacandin class antibiotic isolated from Pestalotiopsis humus
Katsuyuki Sakai, Takuya Suga, Masato Iwatsuki, Takumi Chinen, Kenichi Nonaka, Takeo Usui, Yukihiro Asami, Satoshi Ōmura, Kazuro Shiomi J Antibiot (Tokyo). 2018 Nov;71(12):1031-1035. doi: 10.1038/s41429-018-0102-7. Epub 2018 Sep 19.
Secondary metabolites of microorganisms have proven to be an excellent source of drugs. We isolated a new antibiotic, named pestiocandin (1), from a culture broth of a filamentous fungus, Pestalotiopsis humus FKI-7473, using a multidrug-sensitive budding yeast, S. cerevisiae 12geneΔ0HSR-iERG6. The structure of 1 was elucidated by various NMR studies. All geometric isomerisms of 1 were shown to be the E-form and two pyranose units of 1 were found to be glucose and galactose types. Compound 1 showed weak growth inhibition against Gram-positive and Gram-negative bacteria, yeasts and a filamentous fungus. It displayed more potent growth inhibition against multidrug-sensitive yeasts than wild-type yeasts.
3. Sharpless asymmetric dihydroxylation of 5-aryl-2-vinylfurans: application to the synthesis of the spiroketal moiety of papulacandin D
D Balachari, G A O'Doherty Org Lett. 2000 Mar 23;2(6):863-6. doi: 10.1021/ol0000253.
[formula: see text] Using the Sharpless catalytic asymmetric dihydroxylation reaction on 5-aryl-2-vinylfurans, diols are produced in high enantioexcess. The resulting diols can be efficiently transformed into the spiroketal ring precursor of the antifungal compound papulacandin D. Stereoselective reduction of this precursor followed by a diastereoselective dihydroxylation completes the synthesis of a mannopyranoside isomer of a papulacandin derivative.
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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 ╳
