Synonym
Salinosporamide B;
IUPAC/Chemical Name
(1R,4R,5S)-1-(((S)-cyclohex-2-en-1-yl)(hydroxy)methyl)-4-ethyl-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione
InChi Key
SCJZQKFFYIGMCI-BOZRLRFCSA-N
InChi Code
InChI=1S/C15H21NO4/c1-3-10-12(18)16-15(13(19)20-14(10,15)2)11(17)9-7-5-4-6-8-9/h5,7,9-11,17H,3-4,6,8H2,1-2H3,(H,16,18)/t9-,10+,11?,14+,15+/m1/s1
SMILES Code
O=C([C@H](CC)[C@]1(C)O2)N[C@@]1(C([C@@H]3C=CCCC3)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
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
279.33
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: Beer LL, Moore BS. Biosynthetic convergence of salinosporamides A and B in the marine actinomycete Salinispora tropica. Org Lett. 2007 Mar 1;9(5):845-8. Epub 2007 Feb 3. PubMed PMID: 17274624.
2: Dineshkumar K, Vasudevan A, Hopper W. Ligand Based-Pharmacophore Modeling and Extended Bi oactivity Prediction for Salinosporamide A, B and C from Marine Actino mycetes Salinispora tropica. Comb Chem High Throughput Screen. 2017;20(1):3-19. doi: 10.2174/1386207319666161215154128. PubMed PMID: 28000560.
3: Manam RR, Macherla VR, Tsueng G, Dring CW, Weiss J, Neuteboom ST, Lam KS, Potts BC. Antiprotealide is a natural product. J Nat Prod. 2009 Feb 27;72(2):295-7. doi: 10.1021/np800578e. PubMed PMID: 19133779.
4: Tsueng G, McArthur KA, Potts BC, Lam KS. Unique butyric acid incorporation patterns for salinosporamides A and B reveal distinct biosynthetic origins. Appl Microbiol Biotechnol. 2007 Jul;75(5):999-1005. Epub 2007 Mar 6. PubMed PMID: 17340108.
5: Williams PG, Buchanan GO, Feling RH, Kauffman CA, Jensen PR, Fenical W. New cytotoxic salinosporamides from the marine Actinomycete Salinispora tropica. J Org Chem. 2005 Aug 5;70(16):6196-203. PubMed PMID: 16050677.
6: Reed KA, Manam RR, Mitchell SS, Xu J, Teisan S, Chao TH, Deyanat-Yazdi G, Neuteboom ST, Lam KS, Potts BC. Salinosporamides D-J from the marine actinomycete Salinispora tropica, bromosalinosporamide, and thioester derivatives are potent inhibitors of the 20S proteasome. J Nat Prod. 2007 Feb;70(2):269-76. Epub 2007 Jan 23. PubMed PMID: 17243724.
7: Tsueng G, Lam KS. A low-sodium-salt formulation for the fermentation of salinosporamides by Salinispora tropica strain NPS21184. Appl Microbiol Biotechnol. 2008 Apr;78(5):821-6. doi: 10.1007/s00253-008-1357-x. Epub 2008 Feb 1. PubMed PMID: 18239916.
8: Eustáquio AS, Moore BS. Mutasynthesis of fluorosalinosporamide, a potent and reversible inhibitor of the proteasome. Angew Chem Int Ed Engl. 2008;47(21):3936-8. doi: 10.1002/anie.200800177. PubMed PMID: 18407559.
9: Tsueng G, Sing Lam K. Effect of cobalt and vitamin B12 on the production of salinosporamides by Salinispora tropica. J Antibiot (Tokyo). 2009 Apr;62(4):213-6. doi: 10.1038/ja.2009.7. Epub 2009 Feb 6. PubMed PMID: 19198638.
