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MedKoo Cat#: 596605 | Name: Preussin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Preussin is a new hydroxypyrrolidine alkaloid isolated from Aspergillus ochraceus.

Chemical Structure

Preussin
CAS#119463-16-0

Theoretical Analysis

MedKoo Cat#: 596605

Name: Preussin

CAS#: 119463-16-0

Chemical Formula: C21H35NO

Exact Mass: 317.2719

Molecular Weight: 317.51

Elemental Analysis: C, 79.44; H, 11.11; N, 4.41; O, 5.04

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Preussin; L-657,398; L 657,398; L657,398;
IUPAC/Chemical Name
2-benzyl-1-methyl-5-nonylpyrrolidin-3-ol
InChi Key
GBCXKHLKJHRTAB-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H35NO/c1-3-4-5-6-7-8-12-15-19-17-21(23)20(22(19)2)16-18-13-10-9-11-14-18/h9-11,13-14,19-21,23H,3-8,12,15-17H2,1-2H3
SMILES Code
OC1C(CC2=CC=CC=C2)N(C)C(CCCCCCCCC)C1
Appearance
Solid powder
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
>2 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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 317.51 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.

Recalculate based on batch purity %
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: Buttachon S, Ramos AA, Inácio Â, Dethoup T, Gales L, Lee M, Costa PM, Silva AMS, Sekeroglu N, Rocha E, Pinto MMM, Pereira JA, Kijjoa A. Bis-Indolyl Benzenoids, Hydroxypyrrolidine Derivatives and Other Constituents from Cultures of the Marine Sponge-Associated Fungus Aspergillus candidus KUFA0062. Mar Drugs. 2018 Apr 6;16(4). pii: E119. doi: 10.3390/md16040119. PubMed PMID: 29642369; PubMed Central PMCID: PMC5923406. 2: Mao H, Jeong H, Yang J, Ha HJ, Yang JW. Preparation of Chiral Contiguous Epoxyaziridines and Their Regioselective Ring-Opening for Drug Syntheses. Chemistry. 2018 Feb 16;24(10):2370-2374. doi: 10.1002/chem.201706161. Epub 2018 Jan 25. PubMed PMID: 29314353. 3: Rong HJ, Yao JJ, Li JK, Qu J. Molecular Iodine-Mediated α-C-H Oxidation of Pyrrolidines to N,O-Acetals: Synthesis of (±)-Preussin by Late-Stage 2,5-Difunctionalizations of Pyrrolidine. J Org Chem. 2017 Jun 2;82(11):5557-5565. doi: 10.1021/acs.joc.7b00361. Epub 2017 May 18. PubMed PMID: 28497692. 4: Si CM, Shao LP, Mao ZY, Zhou W, Wei BG. An efficient approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones through a stereoselective tandem Barbier process: divergent syntheses of (3R,4S)-statines, (+)-preussin and (-)-hapalosin. Org Biomol Chem. 2017 Jan 18;15(3):649-661. doi: 10.1039/c6ob02523d. PubMed PMID: 27973631. 5: Buchman M, Csatayová K, Davies SG, Fletcher AM, Houlsby IT, Roberts PM, Rowe SM, Thomson JE. Asymmetric Syntheses of (+)-Preussin B, the C(2)-Epimer of (-)-Preussin B, and 3-Deoxy-(+)-preussin B. J Org Chem. 2016 Jun 17;81(12):4907-22. doi: 10.1021/acs.joc.6b00362. Epub 2016 May 13. PubMed PMID: 27077325. 6: Rosset IG, Dias RM, Pinho VD, Burtoloso AC. Three-step synthesis of (±)-preussin from decanal. J Org Chem. 2014 Jul 18;79(14):6748-53. doi: 10.1021/jo5011558. Epub 2014 Jul 8. PubMed PMID: 24979222. 7: Fukuda T, Sudoh Y, Tsuchiya Y, Okuda T, Igarashi Y. Isolation and biosynthesis of preussin B, a pyrrolidine alkaloid from Simplicillium lanosoniveum. J Nat Prod. 2014 Apr 25;77(4):813-7. doi: 10.1021/np400910r. Epub 2014 Mar 4. PubMed PMID: 24588303. 8: Natori Y, Kikuchi S, Kondo T, Saito Y, Yoshimura Y, Takahata H. Asymmetric synthesis of 2,5-disubstituted 3-hydroxypyrrolidines based on stereodivergent intramolecular iridium-catalyzed allylic aminations. Org Biomol Chem. 2014 Mar 28;12(12):1983-94. doi: 10.1039/c3ob42229a. Epub 2014 Feb 19. PubMed PMID: 24549243. 9: Xiao KJ, Wang Y, Ye KY, Huang PQ. Versatile one-pot reductive alkylation of lactams/amides via amide activation: application to the concise syntheses of bioactive alkaloids (±)-bgugaine, (±)-coniine, (+)-preussin, and (-)-cassine. Chemistry. 2010 Nov 15;16(43):12792-6. doi: 10.1002/chem.201002054. PubMed PMID: 20938943. 10: Draper JA, Britton R. A concise and stereoselective synthesis of hydroxypyrrolidines: rapid synthesis of (+)-preussin. Org Lett. 2010 Sep 17;12(18):4034-7. doi: 10.1021/ol101631e. PubMed PMID: 20726562. 11: Chowdhury R, Ghosh SK. Highly regio- and enantioselective organocatalytic conjugate addition of alkyl methyl ketones to a beta-silylmethylene malonate. Org Lett. 2009 Aug 6;11(15):3270-3. doi: 10.1021/ol900803n. PubMed PMID: 19580247. 12: Davis FA, Zhang J, Qiu H, Wu Y. Asymmetric synthesis of cis- and trans-2,5-disubstituted pyrrolidines from 3-oxo pyrrolidine 2-phosphonates: synthesis of (+)-preussin and analogs. Org Lett. 2008 Apr 3;10(7):1433-6. doi: 10.1021/ol800255r. Epub 2008 Mar 11. PubMed PMID: 18331047. 13: Bertrand MB, Wolfe JP. A concise stereoselective synthesis of Preussin, 3-epi-Preussin, and analogues. Org Lett. 2006 May 25;8(11):2353-6. PubMed PMID: 16706524; PubMed Central PMCID: PMC2613785. 14: Huang PQ, Wu TJ, Ruan YP. A flexible approach to (S)-5-alkyl tetramic acid derivatives: application to the asymmetric synthesis of (+)-preussin and protected (3S,4S)-AHPPA. Org Lett. 2003 Nov 13;5(23):4341-4. PubMed PMID: 14601995. 15: Goss Kinzy T, Harger JW, Carr-Schmid A, Kwon J, Shastry M, Justice M, Dinman JD. New targets for antivirals: the ribosomal A-site and the factors that interact with it. Virology. 2002 Aug 15;300(1):60-70. PubMed PMID: 12202206. 16: Okue M, Watanabe H, Kasahara K, Yoshida M, Horinouchi S, Kitahara T. Short-step syntheses of all stereoisomers of preussin and their bioactivities. Biosci Biotechnol Biochem. 2002 May;66(5):1093-6. PubMed PMID: 12092820. 17: Lee KY, Kim YH, Oh CY, Ham WH. Facile and efficient total synthesis of (+)-preussin. Org Lett. 2000 Dec 14;2(25):4041-2. PubMed PMID: 11112638. 18: Bach T, Brummerhop H, Harms K. The synthesis of (+)-preussin and related pyrrolidinols by diastereoselective Paternò-Büchi reactions of chiral 2-substituted 2,3-dihydropyrroles. Chemistry. 2000 Oct 16;6(20):3838-48. PubMed PMID: 11073254. 19: Achenbach TV, Slater EP, Brummerhop H, Bach T, Müller R. Inhibition of cyclin-dependent kinase activity and induction of apoptosis by preussin in human tumor cells. Antimicrob Agents Chemother. 2000 Oct;44(10):2794-801. PubMed PMID: 10991862; PubMed Central PMCID: PMC90153. 20: Bach T, Brummerhop H. Unprecedented Facial Diastereoselectivity in the Paternò-Büchi Reaction of a Chiral Dihydropyrrole-A Short Total Synthesis of (+)-Preussin. Angew Chem Int Ed Engl. 1998 Dec 31;37(24):3400-3402. doi: 10.1002/(SICI)1521-3773(19981231)37:24<3400::AID-ANIE3400>3.0.CO;2-3. PubMed PMID: 29711279.

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PRGL493

PRGL493