Pteridic acid A
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| Category | Others |
| Catalog number | BBF-02071 |
| CAS | |
| Molecular Weight | 364.47 |
| Molecular Formula | C21H32O5 |
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Description
Pteridic acid A is a plant growth promoter produced by Streptomyces hygrescopicus TP-A0451. It has Auxin-like plant growth hormone activity, and 1 nmol/L can promote the growth of legumes and other plant roots.
Specification
| IUPAC Name | (2E,4E,6S)-6-[(2S,3S,4R,5R,6R,8R,9S)-9-ethyl-4-hydroxy-3,5,8-trimethyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl]hepta-2,4-dienoic acid |
| Canonical SMILES | CCC1C=CC2(C(C(C(C(O2)C(C)C=CC=CC(=O)O)C)O)C)OC1C |
| InChI | InChI=1S/C21H32O5/c1-6-17-11-12-21(25-16(17)5)15(4)19(24)14(3)20(26-21)13(2)9-7-8-10-18(22)23/h7-17,19-20,24H,6H2,1-5H3,(H,22,23)/b9-7+,10-8+/t13-,14-,15+,16+,17-,19+,20-,21+/m0/s1 |
| InChI Key | QBUNWYIRJPTIPL-KJDSHMCHSA-N |
Properties
| Appearance | Light Yellow Oil |
| Boiling Point | 536.1±50.0°C at 760 mmHg |
| Density | 1.1±0.1 g/cm3 |
Reference Reading
1. Total synthesis of pteridic acids A and B
Luiz C Dias, Airton G Salles J Org Chem. 2009 Aug 7;74(15):5584-9. doi: 10.1021/jo9010365.
The total synthesis of pteridic acids A and B is reported. The convergent asymmetric synthesis involved the use of a diastereoselective ethyl ketone aldol reaction followed by an efficient spiroketalization and provided pteridic acids A and B in 2.9% and 2.8% overall yield, respectively.
2. Pteridic acid hydrate and pteridic acid C produced by StreStreptomyces pseudoverticillus YN17707 induce cell cycle arrest
Bing Han, Wen-Xin Li, Cheng-Bin Cui Chin J Nat Med. 2015 Jun;13(6):467-70. doi: 10.1016/S1875-5364(15)30041-8.
The present study aimed at identifying cell cycle inhibitors from the fermentation broth of Streptomyces pseudoverticillus YN17707. Activity-guided isolation was performed on tsFT210 cells. Compounds were isolated through various chromatographic methods and elucidated by spectroscopic analyses. Flow cytometry was used to evaluate the cell cycle inhibitory activities of the fractions and compounds. Two compounds were obtained and identified as pteridic acid hydrate (1) and pteridic acid C (2), which arrested the tsFT210 cells at the G0/G1 phase with the MIC values being 32.8 and 68.9 μmol·L(-1), respectively. These results provide a basis for future development of Compounds 1 and 2 as novel cell cycle inhibitors for cancer therapy.
3. Total synthesis of pteridic acid A
J S Yadav, V Rajender, Y Gangadhara Rao Org Lett. 2010 Jan 15;12(2):348-50. doi: 10.1021/ol9026842.
A convergent approach to the total synthesis of pteridic acid A, having potent plant growth regulator activity, is described. Key steps include the desymmetrization of bicyclic olefin with Brown's chiral hydroboration, acid-mediated spiroketalization, and zirconium-catalyzed ethylmagnesation protocol to install the ethyl stereocenter at C14.
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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 ╳
