Synonym
Korupensamine A; Korupensamine;
IUPAC/Chemical Name
6,8-Isoquinolinediol, 1,2,3,4-tetrahydro-5-(4-hydroxy-5-methoxy-7-methyl-1-naphthalenyl)-1,3-dimethyl-, (1R,3R,5S)-
InChi Key
JOXWHCNNDTWJPX-CHWSQXEVSA-N
InChi Code
InChI=1S/C23H25NO4/c1-11-7-15-14(5-6-17(25)23(15)20(8-11)28-4)22-16-9-12(2)24-13(3)21(16)18(26)10-19(22)27/h5-8,10,12-13,24-27H,9H2,1-4H3/t12-,13-/m1/s1
SMILES Code
OC1=[C@]([C@]2=C3C=C(C)C=C(OC)C3=C(O)C=C2)C4=C([C@@H](C)N[C@H](C)C4)C(O)=C1
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
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
379.46
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: Xu G, Fu W, Liu G, Senanayake CH, Tang W. Efficient syntheses of korupensamines A, B and michellamine B by asymmetric Suzuki-Miyaura coupling reactions. J Am Chem Soc. 2014 Jan 15;136(2):570-3. doi: 10.1021/ja409669r. Epub 2013 Oct 28. PubMed PMID: 24147559.
2: Lipshutz BH, Keith JM. A Stereospecific, Intermolecular Biaryl-Coupling Approach to Korupensamine A En Route to the Michellamines. Angew Chem Int Ed Engl. 1999 Dec 3;38(23):3530-3533. PubMed PMID: 10602232.
3: Bringmann G, Messer K, Brun R, Mudogo V. Ancistrocongolines A-D, new naphthylisoquinoline alkaloids from ancistrocladus congolensis. J Nat Prod. 2002 Aug;65(8):1096-101. PubMed PMID: 12193010.
4: Huang S, Petersen TB, Lipshutz BH. Total synthesis of (+)-korupensamine B via an atropselective intermolecular biaryl coupling. J Am Chem Soc. 2010 Oct 13;132(40):14021-3. doi: 10.1021/ja1065202. PubMed PMID: 20849111.
5: Bringmann G, Günther C, Saeb W, Mies J, Wickramasinghe A, Mudogo V, Brun R. Ancistrolikokines A-C: new 5,8'-coupled naphthylisoquinoline alkaloids from Ancistrocladus likoko. J Nat Prod. 2000 Oct;63(10):1333-7. PubMed PMID: 11076547.
6: Watanabe T, Tanaka Y, Shoda R, Sakamoto R, Kamikawa K, Uemura M. Stereoselective synthesis of atropisomeric korupensamines A and B utilizing planar chiral arene chromium complex. J Org Chem. 2004 Jun 11;69(12):4152-8. PubMed PMID: 15176842.
7: Schlauer J, Rückert M, Wiesen B, Herderich M, Assi LA, Haller RD, Bär S, Fröhlich KU, Bringmann G. Characterization of enzymes from Ancistrocladus (Ancistrocladaceae) and Triphyophyllum (Dioncophyllaceae) catalyzing oxidative coupling of naphthylisoquinoline alkaloids to michellamines. Arch Biochem Biophys. 1998 Feb 1;350(1):87-94. PubMed PMID: 9466824.
8: Bringmann G, Ochse M, Götz R. First atropo-divergent total synthesis of the antimalarial korupensamines A and B by the "lactone method". J Org Chem. 2000 Apr 7;65(7):2069-77. PubMed PMID: 10774027.
