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

View Publications

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
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
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
Butcher, R.A., M. Fujita, F.C. Schroeder & J. Clardy. 2007. Small-molecule pheromones that control dauer development in Caenorhabditis elegans. Nat. Chem. Biol. : 420-422
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
Spiegel, D.A., F.C.. Schroeder and S.L. Schreiber. 2006. An oligomerization approach to generating skeletal diversity. J. Am. Chem. Soc. 128(46): 14766-14767
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., M. Gronquist. 2006. Extending the scope of NMR spectroscopy with microcoil probes. Angew. Chem. Int. Ed. 45: 7122-7131
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
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(42): 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
Schroeder, Frank C, . 2006. Small molecule signaling in Caenorhabditis elegans. ACS Chem. Biol. 1: 198-200
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
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
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 : 463-476
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
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. : 34-47
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(9): 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(10): 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. : 1745-1748
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
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
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(17): 5896-5900
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
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
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
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
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
Farmer, J.J., F.C. Schroeder, J. Meinwald. 2000. Synthesis of macrocyclic insect-derived alkaloids. Helv. Chim. Acta : 2594-2606
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
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.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
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
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., W. Francke. 1998. Synthesis of myrmicarin 217, a Pyrrolo[2,1,5-cd]indolizidine from ants. Tetrahedron 54: 5259-5264
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
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, 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. : 2139-2140
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. : 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. : 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. : 1211-1218