Griseolic acid B
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01286 |
| CAS | 98890-01-8 |
| Molecular Weight | 363.28 |
| Molecular Formula | C14H13N5O7 |
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Description
It is produced by the strain of Streptomyces griseoaurantiacus SANK43894. It has the activity of inhibiting cyclic adenosine monophosphate (cAMP) phosphodiesterase [EC 3.1.4.17] with IC50 0.16 X 10-6 mol/L (Extracted from rat brain).
Specification
| Synonyms | (2R,5R,6R,6aS)-5-(6-amino-9H-purin-9-yl)-2-(carboxymethyl)-6-hydroxy-2,5,6,6a-tetrahydrofuro[3,2-b]furan-2-carboxylic acid; Deoxygriseolic Acid; 1-(6-Amino-9H-purin-9-yl)-3,6-anhydro-6-C-carboxy-1,5,7-trideoxy-β-D-ribo-4-octenofuranuronic acid; 7'-Desoxygriseolic acid |
| IUPAC Name | (2R,3R,3aS,5R)-2-(6-aminopurin-9-yl)-5-(carboxymethyl)-3-hydroxy-3,3a-dihydro-2H-furo[3,2-b]furan-5-carboxylic acid |
| Canonical SMILES | C1=C2C(C(C(O2)N3C=NC4=C(N=CN=C43)N)O)OC1(CC(=O)O)C(=O)O |
| InChI | InChI=1S/C14H13N5O7/c15-10-7-11(17-3-16-10)19(4-18-7)12-8(22)9-5(25-12)1-14(26-9,13(23)24)2-6(20)21/h1,3-4,8-9,12,22H,2H2,(H,20,21)(H,23,24)(H2,15,16,17)/t8-,9-,12-,14+/m1/s1 |
| InChI Key | WRHIKWNGCJVUOW-MGGABWITSA-N |
Properties
| Appearance | White Powder |
| Boiling Point | 889.2 °C at 760 mmHg |
| Melting Point | 160 °C |
| Density | 2.13 g/cm3 |
| Solubility | Soluble in Water, DMSO |
Reference Reading
1. Synthesis of griseolic acid B by pi-face-dependent radical cyclization
S Knapp, M R Madduru, Z Lu, G J Morriello, T J Emge, G A Doss Org Lett. 2001 Nov 1;3(22):3583-5. doi: 10.1021/ol0167210.
[reaction: see text]. Radical cyclization of 6 affords the bicyclic vinyl ether 9 with the appropriate stereochemistry for elaboration (seven steps) to griseolic acid B (1).
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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 ╳
