Synonym
Asperparaline A, Aspergillimide, VM 55598
IUPAC/Chemical Name
(1R,3'R,5aR,8aR,9aS)-rel-(-)-tetrahydro-1,1',8,8,11-pentamethyl-spiro[5H,6H-5a,9a-(iminomethano)-1H-cyclopent[f]indolizine-7(8H),3'-pyrrolidine]-2',5',10-trione
InChi Key
RTNMRJRMTGSUAE-UXVBPGSQSA-N
InChi Code
InChI=1S/C20H29N3O3/c1-12-6-7-23-11-19-10-18(9-14(24)21(4)15(18)25)17(2,3)13(19)8-20(12,23)16(26)22(19)5/h12-13H,6-11H2,1-5H3/t12-,13-,18-,19+,20?/m0/s1
SMILES Code
O=C(C1)N(C)C([C@@]21C(C)(C)[C@]3([H])CC45N(CC[C@@H]4C)C[C@]3(N(C)C5=O)C2)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
359.47
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Ezekiel CN, Kraak B, Sandoval-Denis M, Sulyok M, Oyedele OA, Ayeni KI, Makinde OM, Akinyemi OM, Krska R, Crous PW, Houbraken J. Diversity and toxigenicity of fungi and description of Fusarium madaense sp. nov. from cereals, legumes and soils in north-central Nigeria. MycoKeys. 2020 Jun 8;67:95-124. doi: 10.3897/mycokeys.67.52716. PMID: 32565683; PMCID: PMC7295817.
2: Crick PJ, Simpkins NS, Highton A. Synthesis of the asperparaline core by a radical cascade. Org Lett. 2011 Dec 16;13(24):6472-5. doi: 10.1021/ol202769f. Epub 2011 Nov 14. PMID: 22082317.
3: Hirata K, Kataoka S, Furutani S, Hayashi H, Matsuda K. A fungal metabolite asperparaline a strongly and selectively blocks insect nicotinic acetylcholine receptors: the first report on the mode of action. PLoS One. 2011 Apr 1;6(4):e18354. doi: 10.1371/journal.pone.0018354. PMID: 21483774; PMCID: PMC3069973.
4: Gray CR, Sanz-Cervera JF, Silks LA, Williams RM. Studies on the biosynthesis of asperparaline A: origin of the spirosuccinimde ring system. J Am Chem Soc. 2003 Dec 3;125(48):14692-3. doi: 10.1021/ja037687i. PMID: 14640629.
5: Williams RM, Cox RJ. Paraherquamides, brevianamides, and asperparalines: laboratory synthesis and biosynthesis. An interim report. Acc Chem Res. 2003 Feb;36(2):127-39. doi: 10.1021/ar020229e. PMID: 12589698.
6: Williams RM. Total synthesis and biosynthesis of the paraherquamides: an intriguing story of the biological Diels-Alder construction. Chem Pharm Bull (Tokyo). 2002 Jun;50(6):711-40. doi: 10.1248/cpb.50.711. PMID: 12045324.
7: Tanimori S, Fukubayashi K, Kirihata M. Synthesis of the spirosuccinimide moiety of Asperparaline A. Biosci Biotechnol Biochem. 2000 Aug;64(8):1758-60. doi: 10.1271/bbb.64.1758. PMID: 10993171.
8: Hayashi H, Nishimoto Y, Akiyama K, Nozaki H. New paralytic alkaloids, asperparalines A, B and C, from Aspergillus japonicus JV-23. Biosci Biotechnol Biochem. 2000 Jan;64(1):111-5. doi: 10.1271/bbb.64.111. PMID: 10705455.
9: Banks RM, Blanchflower SE, Everett JR, Manger BR, Reading C. Novel anthelmintic metabolites from an Aspergillus species; the aspergillimides. J Antibiot (Tokyo). 1997 Oct;50(10):840-6. doi: 10.7164/antibiotics.50.840. PMID: 9402989.
