Frank C. Schroeder

Frank C. Schroeder

Assistant Scientist

Office/Lab: Room 425 /414-420

Contact: fs31@cornell.edu / 607 254-4391 fax 607 254 2958

Affiliations:

Department of Chemistry and Chemical Biology, Cornell University

Research Summary

Our research is directed at characterizing structures and biological function of natural products, often referred to as secondary metabolites. The potential of natural products to serve as tools for understanding biological processes at the molecular level and to provide lead structures for the design of new pharmaceuticals to fight human disease is undisputed. Considering their origin in living organisms, natural products must have evolved to serve biological functions. This evolutionary history has resulted in small molecules with useful affinities for specific molecular targets. Nature uses a distinct approach to create such molecules, and biosynthesis often differs in its fundamental logic from laboratory synthesis.

We are particularly interested in improving methods for the detection and structural characterization of natural products. Usually, natural products occur as - often minor - components of a more or less complex biological matrix, which necessitates the use of time-consuming and lossy fractionation procedures for their isolation. Reducing the dependency on fractionation would increase the realm of accessible natural products and aid with determining their biological roles. One of our aims is to develop NMR-based approaches that will enable detailed characterization of secondary metabolites in native or marginally fractionated biological extracts. Using this methodology we pursue the biosynthesis and identification of new polyketides from Bacillus, combinatorial fermentation of fungi, small-molecule signaling in the nematode Caenorhabditis elegans, as well as compounds mediating chemical defense in arthropods. Check out our research pages for details.


Publications

Butcher, R.A., M. Fujita, F.C. Schroeder & J. Clardy. 2007. Small-molecule pheromones that control dauer development in Caenorhabditis elegans. Nat. Chem. Biol. 0: 420-422

Schroeder, F.C., D.M. Gibson, A.C.L. Churchill, E.J. Wursthorn, S.B. Krasnoff, and J. Clardy. 2007. New natural products from a pilot-scale fungal extract library. Angew Chem. Int. Ed. 46: 901–904

Butcher, R.A., F.C. Schroeder, M.A. Fischbach, C.T. Walsh, and J. Clardy. 2007. The identification of bacillaene, the product of the PksX megacomplex in Bacillus subtilis. Proc. Natl. Acad. Sci. USA 104: 1506-1509

Hutchinson, D., A. Mori, A. Savitzky, G. Burghardt, X, Wu, J. Meinwald, F.C. Schroeder. 2007. Dietary sequestration of defensive steroids in nuchal glands of the Asian Snake Rhabdophis tigrinus. Proc. Natl. Acad. Sci. USA 104: 2265-2270

Chatterjee, A., C.T. Jurgenson, F.C. Schroeder, S.E. Ealick, and T.P. Begley. 2007. Biosynthesis of thiamin thiazole in eukaryotes: Conversion of NAD to an advanced intermediate. J. Am. Chem. Soc. 129: 2914-2922

Schroeder, F.C., D.M. Gibson, A.C.L. Churchill, E.J. Wursthorn, S.B. Krasnoff, and J. Clardy. 2007. Differential analysis of 2D NMR spectra: New natural products from a pilot-scale fungal extract library. Angew. Chem. Int. Ed. 46: 901 –904

Spiegel, D.A., F.C.. Schroeder and S.L. Schreiber. 2006. An oligomerization approach to generating skeletal diversity. J. Am. Chem. Soc. 128: 14766-14767

Schroeder, F.C., M. Gronquist. 2006. Extending the scope of NMR spectroscopy with microcoil probes. Angew. Chem. Int. Ed. 45: 7122-7131

Chatterjee, A., C.T. Jurgenson, F.C. Schroeder, S.E. Ealick, T.P. Begley. 2006. Thiamin biosynthesis in eukaryotes: Characterization of the enzyme-bound product of thiazole synthase from Saccharomyces cerevisiae and its implications in thiazole biosynthesis. J. Am. Chem. Soc. 128: 7158-7159

Schroeder, Frank C, . 2006. Small molecule signaling in Caenorhabditis elegans. ACS Chem. Biol. 1: 198-200

Maloney, K.N., W. Hao, J. Xu, J. Gibbons, J. Hucul, D. Roll, S.F. Brady, F.C. Schroeder, J. Clardy. 2006. Phaeosphaeride A, An inhibitor of STAT3-dependent signaling isolated from an endophytic fungus. Org. Lett. 8: 4067-4070

Ueki, M., D.P. Galonić, F.H. Vaillancourt, S. Garneau-Tsodikova, E. Yeh, D.A. Vosburg, F.C. Schroeder, H. Osada, C.T. Walsh. 2006. Enzymatic generation of the antimetabolite γ,γ-dichloroaminobutyrate by NRPS and mononuclear iron halogenase action in a streptomycete. Chem. Biol. 13: 1183-1191

Schroeder, F.C, J.B. Grant, D.B. Weibel, S.R. Smedley, K.L. Bolton, J. Meinwald, T. Eisner. 2006. Pinoresinol: a basic lignol of plant origin, appropriated for defensive purposes by a caterpillar. Proc. Natl. Acad. Sci. 103: 15497-15501

Gronquist, M., F.C. Schroeder, H. Ghiradella, D. Hill, E.M. McCoy, J. Meinwald and T. Eisner. 2006. Shunning the night to elude the hunter: diurnal fireflies and the “femmes fatales”. Chemoecology 16: 10810-10811

Gronquist, M, J. Meinwald, T. Eisner, F.C. Schroeder. 2005. Exploring uncharted terrain in nature's structure space using capillary NMR spectroscopy: 13 steroids from 50 fireflies. J. Am. Chem. Soc. 127: 10810-10811

Schroeder, F.C., T.R. Kau, P.A. Silver, J. Clardy. 2005. The psammaplysenes, specific inhibitors of FOXO1a nuclear export. J. Nat. Prod. 68: 574

Taggi, A.E., J. Meinwald, F.C. Schroeder. 2004. A new approach to natural products discovery exemplified by the identification of sulfated nucleosides in spider venom. J. Am. Chem. Soc. 126: 10364-10369

Schroeder, F.C, D.B. Weibel, J. Meinwald. 2004. Chiral silylation reagents: Determining configuration via NMR-spectroscopic co-analysis. Org. Lett, 6: 3019-3022

Yack, J. E., W.E. Conner, T.A. Timbers, A. Aiello, F.C. Schroeder. 2003. Defensive ‘flocculent’ emissions in a Tiger moth, Homoeocera stictosoma (Arctiidae, Actiinae). J. Lep. Soc. 0: 34-47

Kau, T.R., F.C. Schroeder, C.L. Wojciechowski, J.J. Zhou, T. Roberts, J. Clardy, W.R. Sellers, P.A. Silver. 2003. A chemical genetic screen identifies inhibitors of regulated nuclear export of a Forkhead transcription factor in PTEN-deficient tumor cells. Cancer Cell 0: 463-476

Tsao, R., A.B. Attygalle, F.C. Schroeder, C.H. Marvin, B.D. McGarvey. 2003. Isobutylamides of unsaturated fatty acids from chrysanthemum morifolium associated with host-plant resistance against the Western Flower Thrips. J. Natl. Prod. 66: 1229-1231

McGarvey, B.D., A.B. Attygalle, A.N. Starratt, J.E. Brandle, B. Xiang, F.C. Schroeder, and J. Meinwald. 2003. New non-glycosidic diterpenes from leaves of Stevia rebaudiana. J. Nat. Prod. 66: 1395-1398

Williamson, R.T., A.C. Barrios Sosa, A. Mitra, P.J. Seaton, D.B. Weibel, F.C. Schroeder. 2003. New silyl ether reagents for the absolute stereochemical determination of secondary alcohols. Org. Lett. 0: 1745-1748

Roque-Albelo, L., F.C. Schroeder, W.E. Conner, A. Bezzerides, E.R. Hoebeke, J. Meinwald, T. Eisner. 2003. Chemical defense and aposematism: the case of Utetheisa galapagensis. Chemoecology 12: 153-157

Weibel, D.B., L.E. Shevy, F.C. Schroeder, J. Meinwald. 2002. Synthesis of Mayolene-16 and Mayolene-18: Larval defensive lipids from the European Cabbage Butterfly. J. Org. Chem. 67: 5896-5900

Smedley, S.R., F.C. Schroeder, D.B. Weibel, J. Meinwald, K.A. Lafleur, J.A. Renwick, R. Rutowski, and T. Eisner. 2002. Mayolenes: Labile defensive lipids from the glandular hairs of a caterpillar (Pieris rapae). Proc. Natl. Acad. Sci. USA 99: 6822-6827

Reinhard, J., M.J. Lacey, F. Ibarra, F. Schroeder, M. Kaib, M. Lenz. 2002. Hydroquinone: a general phagostimulating pheromone in termites. J. Chem. Ecol. 28: 1-14

Reinhard, J., M.J. Lacey, F. Ibarra, F. Schroeder, M. Kaib, M. Lenz. 2002. Hydroquinone: a general phagostimulating pheromone in termites. J. Chem. Ecol. 28: 1-14

Darling, D.C., F.C. Schroeder, J. Meinwald, M. Eisner, T. Eisner. 2001. Production of a cyanogenic secretion by a thyridid caterpillar. Naturwissenschaften 88: 306-309

del Campo, M.L., C.I. Miles, F.C. Schroeder, C. Mueller, R. Booker, J.A. Renwick. 2001. Host recognition by the tobacco hornworm is mediated by a host plant compound. Nature 411: 186-189

Conner, W.E., R. Boada, F.C. Schroeder, A. Gonzales, J. Meinwald, T. Eisner,. 2000. Chemical defense: bestowal of a nuptial alkaloidal garment by a male moth upon its mate. Proc. Natl. Acad. Sci. USA 97: 14406-14411

Farmer, J.J., F.C. Schroeder, J. Meinwald. 2000. Synthesis of macrocyclic insect-derived alkaloids. Helv. Chim. Acta 0: 2594-2606

Schroeder. F.C., J.J. Farmer, A.B. Attygalle, S.R. Smedley, T. Eisner, and J. Meinwald. 2000. A combinatorial library of macrocyclic polyamines produced by a ladybird beetle . J. Am. Chem. 122: 3628-3634

Weibel, D. B., T.R. Walker, F.C. Schroeder, J. Meinwald. 2000. Chiral silylation reagents for the determination of absolute configuration by NMR spectroscopy. Org. Lett. 2: 2381-2383

Gonzales, A., F.C. Schroeder, A.B. Attygalle, A. Svatos, J. Meinwald, T. Eisner. 1999. Metabolic transformations of acquired lucibufagins by firefly "femmes fatales". Chemoecology 9: 105-112

Schroeder, F.C., A. Gonzalez, T. Eisner, and J. Meinwald. 1999. Miriamin, a defensive diterpene from the eggs of a land slug (Arion sp.). Proc. Natl. Acad. Sci. USA 96: 13620-13525

Gonzalez, A., F.C. Schroeder, T. Eisner, J. Meinwald. 1999. N-Methylquinolinium 2-carboxylate, a defensive betaine from photuris versicolor fireflies. J. Nat. Prod. 62: 378-380

Schröder, F., W. Francke. 1998. Synthesis of myrmicarin 217, a Pyrrolo[2,1,5-cd]indolizidine from ants. Tetrahedron 54: 5259-5264

Subchev, M., A. Harizanov, W. Francke, S. Franke, E. Plass, A. Reckziegel, F. Schröder, J.A. Pickett, L.J. Wadhams, C. M. Woodcock. 1998. Sex pheromone of female Vine Bud Moth, Theresimima ampellophaga, comprises (2S) butyl-(7Z)-tetradecenoate . J. Chem. Ecol. 24: 1141-1152

Schröder, F., . 1998. Induced chemical defense in plants . Angew. Chem. Int. Ed. 37: 1213-1216

Schröder, F.C., S.R. Smedley, L.K. Gibbons, J.J. Farmer, A.B. Attygalle, T. Eisner, J. Meinwald. 1998. Polyazamacrolides from ladybird beetles: Ring-size selective oligomerization. Proc. Natl. Acad. Sci. USA 95: 13387-13391

Schröder, F.C., T. Tolasch. 1998. Psylloborine A, a new dimeric alkaloid from ladybird beetles. Tetrahedron 54: 12243-12248

Schröder. F.C., J.J. Farmer, S.R. Smedley, T. Eisner, and J. Meinwald. 1998. Absolute configuration of the polyazamacrolides, macrocyclic polyamines produced by a ladybird beetle. Tetrahedron Lett. 39: 6625-6628

Schröder, F.C., J.J. Farmer, A.B. Attygalle, S.R. Smedley, T. Eisner, and J. Meinwald. 1998. Combinatorial chemistry in insects: A library of defensive macrocyclic polyamines . Science 281: 428-431

Zeeck, E., C.T. Müller, M. Beckmann, J.D. Hardege, U. Papke, V. Sinnwell, F.C. Schröder, W. Francke. 1998. Cysteine-glutathione disulfide, the sperm-release pheromone of the marine polychaete Nereis succinea(Annelida: Polychaeta) . Chemoecology 8: 33-38

Meinwald, J., Q. Huang, J. Vrkoc, K.B. Herath, Z. Yang, F. Schröder, A.B. Attygalle, V.K. Iyengar, R.C. Morgan, and T. Eisner. 1998. Mirasorvone: A masked 20-ketopregnane from the defensive secretion of a diving beetle (Thermonectus marmoratus). Proc. Natl. Acad. Sci. USA 95: 2733-2737

Schröder, F., V. Sinnwell, H. Baumann, M. Kaib, W. Francke. 1997. Myrmicarin 663: A new decacyclic alkaloid from ants . Angew. Chem. Int. Ed. 36: 77-80

Francke, W., F. Schröder, P. Philipp, H. Meyer, V. Sinnwell, G. Gries. 1996. Identification and synthesis of new bicyclic acetals from the Mountain Pine Beetle, Dendroctonus ponderosae Hopkins (Col.: Scol.). Bioorg. Med. Chem. 4: 363-374

Schröder, F.C., H. Baumann, M. Kaib, V. Sinnwell. 1996. Myrmicarin 430A: a new heptacyclic alkaloid from Myrmicaria ants . Chem. Commun. 0: 2139-2140

Milbrodt, M., F. Schröder, W. A. König. 1996. 3,4-Epoxy-8-deoxycumambrin B, a sesquiterpene lactone from Tanacetum parthenium . Phytochemistry 44: 471-474

Schröder, F., S. Franke, W. Francke, H. Baumann, M. Kaib, J.M. Pasteels, D. Daloze. 1996. A new family of tricyclic alkaloids from Myrmicaria ants. Tetrahedron 52: 13539-13546

Francke, W., F. Schröder, U. Kohnle, M. Simon. 1996. Synthesis of (1S,2R,5R)-2-Ethyl-1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane, the aggregation pheromone of male Beech Bark Beetles, Taphrorychus bicolor (Col., Scol.) . Liebigs Ann. 0: 1523-152

Francke, W., F. Schröder, F. Walter, V. Sinnwell, H. Baumann, M. Kaib. 1995. New alkaloids from ants: Identification and synthesis of (3R,5S,9R)-3-Butyl-5-(1-oxopropyl)-indolizidine and (3R,5R,9R)-3-Butyl-5-(1-oxopropyl)indolizidine, Constituents of the poison gland secretion in Myrmicaria eumenoides (Hymenoptera, Formicidae). Liebigs Ann. 0: 965-977

Francke, W., J. Bartels, H. Meyer, F. Schröder, U. Kohnle, E. Baader, J. P. Vite. 1995. Semiochemicals in Bark Beetles: New results, remarks and reflections . J. Chem. Ecol. 21: 1043-1063

Schroeder, F.C., R. Fettköther, U. Noldt, W.A. König, W. Francke. 1994. Synthesis of (3R)-3-Hydroxy-2 -hexanone, (2R,3R)-2,3-Hexanediol and (2S,3R)-2,3-Hexanediol, the male sex pheromone of Hylotrupes bajulus and Pyrrhidium sanguineum (Cerambycidae). Liebigs Ann. Chem. 0: 1211-1218


Lab Members

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Lab Member
Anna Kurt
Lab Member
Jessica Dawlaty
Lab Member
Chirag Pungaliya