Chemistry and Biochemistry

Merritt B. Andrus

Merritt Andrus

Office: C410 BNSN
Office Phone: 801-422-8171
Lab Room: C476 and C488
Lab Phone: 801-422-9008
Email: mbandrus@chem.byu.edu
Office Hours

Education:

BS, Brigham Young University (1986)

Ph.D., University of Utah (1986-1991)

NIH Postdoctoral Fellow, Harvard University (1991-1993)

Assistant Professor, Purdue University (1993-1997)

Research:

Andrus Lab Group

Efforts in our lab are focused on methods for the synthesis of biologically active natural products that possess unique structures and potential for combinatorial library construction and screening. New methods include metal catalyzed couplings and condensations to assemble key intermediates. Libraries of structural variants are then made and used to probe receptor binding and improve activity.

Recent work includes the synthesis of the polyene stipiamide, a new reversal agent of multidrug resistance (MDR). Various non-natural compounds have been made that restore the potency of cancer drugs to resistant cancer cell lines. New synthetic methods include a copper-tin conjugate addition and palladium acetylene couplings. A combinatorial library, an array of variants using a new solution-phase based approach, has been made and screened based on a simplified stipiamide motif. More potent compounds were identified, and characterized. New oligomeric MDR reversal agents are also under consideration along with photoaffinity labels for the causative MDR protein, Pgp.

Other targets include geldanamycin, a potent anti-cancer agent with a challenging array of functionality. A new anti glycolate asymmetric aldol reaction has been developed to generate the 1,2-methoxy, hydroxy functionality. Computer aided variants will also be made and tested for binding to heat shock protein 90, a key chaperon of oncogenic kinases, and known target for geldanamycin. A far more simple, yet no less important target is the stilbene resveratrol, the suspected causative agent of the 'French Paradox.' Diets rich in foods that contain this material, grapes in particular, lead to lower rates of cancer and heart disease. New coupling methods and strategies were developed to produce this material that will now be used to produce structural variants for various screens. General synthetic methods with broad application are also under development using new ligands for copper. Asymmetric allylic oxidation of olefins using peresters gives allyl ester products in high enantioselectivity. Mechanistic studies and new transformations that have not received great attention in the past are now under study.

Publications:

Andrus, M. B., Lephart, E. D., Acerson, M. J. (2016). Synthesis and skin gene analysis of 4'-acetoxy-resveratrol (4AR), therapeutic potential for dermal applications.. Bioorganic & Medicinal Chemistry Letters, 26, 3258-3262.

Andrus, M. B. (2015). Cinchonanium, 1-(9-anthracenylmethyl)-9-(2-propen-1-yloxy)-, bromide (1:1), (8α,9R). Electronic Encyclopedia of Reagents for Organic Synthesis. New York: Wiley & Sons.

Andrus, M. B., Acerson, M. J., Bingham, B. S., Allred, C. A. (2015). Design and synthesis of terpene based englerin A mimics using chromium oxide mediated remote CH2 oxidation. Tetrahedron Letters , 56(23), 3277-3280.

Andrus, M. B., Acerson, M. J. (2014). Selective esterification of the polyphenol resveratrol at the 4'-position. Tetrahedron Letters , 55(3), 757-760.

Lephart, E. D., Sommerfeldt, J. M., Andrus, M. B. (2014). Resveratrol: influences on gene expression in human skin. Journal of Functional Foods, 10, 377-384.

Andrus, M. B. (2013). (S,S)-2,2'-(dimethylmethylene)bis(4-tert-butyl-2-oxazoline) and (R,R)-2,2'-(dimethylmethylene)bis(4-tert-butyl-2-oxazoline). Handbook of Reagents for Organic Synthesis: Catalytic Oxidation Reagents  (234-257): Wiley and Sons.

Andrus, M. B., Lephart, E. D., Acerson, M. J. (2013). A new synthesis of 4'-resveratrol esters and evaluation of the potential for anti-depressant activity. Bioorganic & Medicinal Chemistry Letters, 23, 2941-2944.

Khosravi, M., Andrus, M. B., Burt, S. R., Woodfield, B. F. (2013). Generalized preparation method and characterization of aluminum isopropoxide, aluminum phenoxide, and aluminum n-hexyloxide. Polyhed., 62, 18-25.

Lephart, E. D., Andrus, M. B. (2013). Resveratrol analogs (butyrate and isobutyrate): human skin gene expression analysis. International Conference of Functional Food Center, 3 (31-35). Dallas, Tx: Gray.

Lephart, E. D., Andrus, M. B. (2012). Gene Science of 4´ Acetoxy Resveratol in Cosmetic Applications. Cosmetic Science, 46 (1, 64).

Cook, T. C., Andrus, M. B., Ess, D. H. (2012). Quantum Mechanical Transition-State Analysis Reveals the Precise Origin of Stereoselectivity in Chiral Quaternary Cinchonidinium Phase-Transfer Catalyzed Enolate Allylation. Organic Letters, 14(23), 5836-5839.

Andrus, M. B., Zhou, Z. (2012). Naphthyl-Substituted Bisoxazoline and Pyridylbisoxazoline-Copper(I) Catalysts for Asymmetric Allylic Oxidation. Tetrahedron Letters, 53, 4518-4521.

Andrus, M. B., Christiansen, M. A. (2012). BOTPPI, a New Wittig Salt for the Synthesis of 12-(S)-Hydroxy-Eicosatetraenoic Acid [12-(S)-HETE]. Tetrahedron Letters, 53, 4805-4808.

Lephart, E. D., Blake, C., Andrus, M. B., Fabick, K. (2012). The Effects of a Resveratrol Derivative on Regulatory Behaviors and Reproductive Health in Female Long-Evans Rats, 32 (1, 1). Washington, D.C.: The Endocrine Society.

Andrus, M. B. (2011). Cinchonanium, 1-(9-anthracenylmethyl)-9-(2-propen-1-yloxy)-, bromide (1:1), (8α,9R). In Rovis, T. (Ed.), Electronic Encyclopedia of Reagents for Organic Synthesis (23): Wiley and Sons.

Andrus, M. B. (2011). Cinchonanium, 10,11-dihydro-9-(2-propen-1-yloxy)-1-[(2,3,4-trifluorophenyl)methyl]-, bromide (1:1), (8α,9R). In Rovis, T. (Ed.), Electronic Encyclopedia of Reagents for Organic Synthesis: Wiley and Sons.

Andrus, M. B. (2011). Allylic and Benzylic Oxidation. In Evans, P. A. (Ed.), Science of Synthesis: Stereoselective Synthesis, 3 (469-482). Stuttgart: Thieme.

Watt, G. D., Hansen, D., Dodson, D., Andrus, M. B., Wheeler, D. R. (2011). Electrical energy from carbohydrate oxidation during viologen-catalyzed O2-oxidation: Mechanistic insights. Renewable Energy, 36(5), 1523-1528. dx.doi.org/10.1016/j.renene.2010.10.016

Andrus, M. B. (2010). Synthesis of 4'-ester analogs of resveratrol and their evaluation in malignant melanoma and pancreatic cell lines. Bioorganic & Medicinal Chemistry Letters, 20(3), 1198-1201.

Andrus, M. B., Wong, Y., Liu, J., Beebe, K., Neckers, L. M. (2009). Synthesis and Evaluation of 8,9-Amido Analogs of Geldanamycin. Tetrahedron Letters, 50, 6705-6708.

Hansen, D., Watt, G. D., Nichols, J., Andrus, M. B., Wheeler, D. R., Choi, S. (2009). Viologen catalysts for a direct carbohydrate fuel cell. Journal of The Electrochemical Society, 156, B1201-B1207. dx.doi.org/10.1149/1.3183815

Andrus, M. B., Harper, K. C., Christiansen, M. A., Binkley, M. A. (2009). Phase-Transfer Catalyzed Asymmetric Arylacetate Alkylation. Tetrahedron Letters, 50, 4541-4544.

Binkley, M., Harper, K., Christiansen, M. A., Andrus, M. B. (2009). Phase-transfer catalyzed asymmetric synthesis of s-naproxen. 237th American Chemical Society National Meeting (ORGN-104). Salt Lake City, UT: 237th ACS National Meeting Book of abstracts,ORGN-104.

Butler, A. W., Clavert, A. L., Binkley, M., Christiansen, M. A., Andrus, M. B. (2009). Phase-transfer catalyzed synthesis of the soy isoflavanoid s-equol. 237th ACS National Meeting (ORGN-105). Salt Lake City, UT: 237th ACS National Meeting Book of abstracts, ORGN-105.

Christiansen, M. A., Andrus, M. B. (2009). Synthesis of 12-HETE using asymmetric phase-transfer catalysis. 237th American Chemical Society National Meeting (ORGN-459). Salt Lake City, UT: 237th ACS National Meeting Book of abstracts, ORGN-459.

Wang, Y., Andrus, M. B., Liu, J. (2009). Synthesis of C8,9-amide geldanamycin analogs. 237th American Chemical Society National Meeting (ORGN-118). Salt Lake City, UT: 237th ACS National Meeting Book of abstracts, ORGN-118.

Nielson, J. R., Andrus, M. B., Christiansen, M. A. (2009). Synthesis of kurasoin b analogs. 237th ACS National Meeting (ORGN-119). Salt Lake City, UT: 237th ACS National Meeting Book of abstracts, ORGN-119.

Christiansen, M. A., Butler, A. W., Hill, A. R., Andrus, M. B. (2009). Synthesis of Kurasoin B Using Phase-Transfer Catalyzed Acylimidazole Alkylation. Synlett, 4, 653-657. www.thieme-connect.de/ejournals/pdf/synlett/doi/10.1055/s-0028-1087809.pdf

Hansen, D., Watt, G. D., Nichols, J., Andrus, M. B., Choi, S., Wheeler, D. R. (2008). Viologen catalyst for direct-carbohydrate fuel cell. 214th Electrochemical Society Meeting, 16 (2057-2063). Honolulu, Hawaii: ECS Transactions.

Stux, A. M., Gorzkowski, E. P., Hansen, D., Watt, G. D., Nichols, J., Andrus, M. B., Wheeler, D. R., Choi, S. (2008). Viologen catalyst for direct-carbohydrate fuel cell. ECS Transactions, 16 (2057-2063).

Andrus, M. B. (2008). Asymmetric Enolate Transformations Under Phase-Transfer Catalysis. Joint 63rd Northwest and 21st Rocky Mountain Regional Meeting of the American Chemical Society (NWRM-057). Park City, UT: Abstracts, Joint 63rd Northwest and 21st Rocky Mountain Regional Meeting.

Andrus, M. B., Christiansen, M. (2008). Asymmetric Glycolate Alkylations with Acylimidazoles. American Chemical Society National Meeting (ORGN-011). New Orleans, LA: Abstracts of Papers, 235th ACS National Meeting.

Andrus, M. B., Ye, Z. (2008). Phase-transfer catalyzed glycolate conjugate addition.. Tetrahedron Letters, 49, 534-537.

Andrus, M. B., Christiansen, M. (2007). Asymmetric Glycolate Alkylations with Acylimidazoles. 232nd ACS National Meeting, Org. Div. #532 (Org. Div. #532). San Francisco, CA,: 232nd ACS National Meeting, Abstracts.

Andrus, M. B., Christiansen, M. A., Hicken, E. J., Gainer, M. J., Bedke, K. D., Harper, K. C., Mikkelson, S. R., Dodson, D. D., Harris, D. V. (2007). Phase-Transfer Catalyzed Asymmetric Acylimidazole Alkylation. Org. Lett., 8, 4865-4868. pubs.acs.org/journals/orlef7/index.html

Woodfield, B. F., Andrus, M. B. (2006). Virtual ChemLab: Organic Synthesis and Organic Qualitative Analysis v2.5.

Andrus, M. B. (2006). Organic Chemistry Study Card to accompany textbook, Paula Bruice, 5th Ed. (8). NY: Pearson.

Andrus, M. B., Hicken, E. J., Bedke, D. K., Christiansen, M. A. (2006). Asymmetric acylimidazole alkylation using phase-transfer catalysis. American Chemical Society (ORGN-505). San Francisco, CA,: Abstract of Papers, 232nd.

Song, C., Chai, Q., Sun, Z., Ma, Y., Ma, C., Zheng, Y., Andrus, M. B. (2006). Asymmetric Allylation of Aldehydes with Allyltrichlorosilane using Aza-Paracyclophane-Oxazoline-N-oxide Catalysts. Tetrahedron Lett., 47, 8611-8615.

Andrus, M. B., Hicken, E. J., Stephens, J. C., Bedko, D. K. (2006). Total Synthesis of the Hydroxyketone Kurasoin A Using Asymmetric Phase-Transfer Alkylation. J. Org. Chem., 71, 8651-8654.

Andrus, M. B., Liu, J. (2006). Synthesis of Polyhydroxylated Ester Analogs of the Stilbene Resveratrol Using Decarbonylative Heck Couplings. Tetrahedron Lett., 47, 5811-5814.

Awards:

Cancer Research Center member