Papulacandin D
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| Category | Antibiotics |
| Catalog number | BBF-02361 |
| CAS | 61036-49-5 |
| Molecular Weight | 574.66 |
| Molecular Formula | C31H42O10 |
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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 | (+)-papulacandin D; (1S,3'R,4'S,5'R,6'R)-3',5,5',7-tetrahydroxy-6'-(hydroxymethyl)-3',4',5',6'-tetrahydro-3H-spiro[2-benzofuran-1,2'-pyran]-4'-yl (2E,4E,7S,8E,10E,14S)-7-hydroxy-8,14-dimethylhexadeca-2,4,8,10-tetraenoate |
| IUPAC Name | [(3S,3'R,4'S,5'R,6'R)-3',4,5',6-tetrahydroxy-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 | CCC(C)CCC=CC=C(C)C(CC=CC=CC(=O)OC1C(C(OC2(C1O)C3=C(CO2)C=C(C=C3O)O)CO)O)O |
| InChI | InChI=1S/C31H42O10/c1-4-19(2)11-7-5-8-12-20(3)23(34)13-9-6-10-14-26(36)40-29-28(37)25(17-32)41-31(30(29)38)27-21(18-39-31)15-22(33)16-24(27)35/h5-6,8-10,12,14-16,19,23,25,28-30,32-35,37-38H,4,7,11,13,17-18H2,1-3H3/b8-5+,9-6+,14-10+,20-12+/t19-,23-,25+,28+,29-,30+,31-/m0/s1 |
| InChI Key | XKSZJTQIZHUMGA-HPZFVNCBSA-N |
Properties
| Appearance | Colorless Amorphous Powder |
| Antibiotic Activity Spectrum | Yeast |
| Boiling Point | 825.5°C at 760 mmHg |
| Melting Point | 127-130°C |
| Density | 1.32 g/cm3 |
| Solubility | Soluble in Chloroform, Methanol, Ethanol, DMF, Ethyl Acetate |
Reference Reading
1. Advances in Pd-catalyzed C-C bond formation in carbohydrates and their applications in the synthesis of natural products and medicinally relevant molecules
Nazar Hussain, Altaf Hussain RSC Adv. 2021 Oct 22;11(54):34369-34391. doi: 10.1039/d1ra06351k. eCollection 2021 Oct 18.
Advances in the Pd-catalyzed synthesis of C-glycosides and branched sugars are summarized herein and the strategies are categorized based on named reactions or types of sugar moieties involved in the reactions. These include cross-coupling reactions, C-H activations, and carbonylative cross-coupling reactions. Applications of Pd-catalyzed C-glycosylation reactions are discussed in the synthesis of natural products and biologically active molecules such as bergenin, papulacandin D, and SGLT2-inhibitors. Important mechanistic cycles are drawn and the mechanisms for how Pd-activates the sugar moieties for various coupling partners are discussed. The directing group-assisted C-glycosylation and some intramolecular C-H activation reactions are also included.
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. Stereocontrolled Synthesis of 2-Fluorinated C-Glycosides
Anna Sadurní, Ryan Gilmour European J Org Chem. 2018 Aug 1;2018(27-28):3684-3687. doi: 10.1002/ejoc.201800618. Epub 2018 Jun 7.
A systematic study of the addition of C-based nucleophiles to fluorinated lactones based on 2-deoxy-2-fluoro-d-pyranoses is disclosed. This high yielding, α-selective process was found to be independent on the nature or configuration [(R)-C(sp3)-F, (S)-C(sp3)-F] of the substituent at C2. Representative, fluorinated analogues of Trehalose, Carminic acid, and the spirocyclic cores of Tofogliflozin and Papulacandin D are also reported. These glycomimics constitute a valuable series of 19F NMR active probes for application in structural biology.
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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 ╳
