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863126-95-8-Salinosporamide B Salinosporamide B

Salinosporamide B

For research use only. Not for therapeutic Use.

  • CAT Number: I035951
  • CAS Number: 863126-95-8
  • Molecular Formula: C15H21NO4
  • Molecular Weight: 279.33
  • Purity: 98%
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Salinosporamide B is a deschloro analog isolated from the marine Actinomycete Salinispora tropica.


Catalog Number I035951
CAS Number 863126-95-8
Synonyms

Salinosporamide B;

Molecular Formula C15H21NO4
Purity 98%
Solubility Soluble in DMSO
Appearance Solid powder
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
IUPAC 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 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
InChIKey SCJZQKFFYIGMCI-BOZRLRFCSA-N
SMILES O=C([C@H](CC)[C@]1(C)O2)N[C@@]1(C([C@@H]3C=CCCC3)O)C2=O
Reference

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.

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