PETER H. SEEBERGER

 

Massachusetts Institute of Technology

Department of Chemistry, Room 18-211

77 Massachusetts Avenue; Cambridge, MA 02139

Tel: (617) 253-3986; Fax: (617) 253-7929

seeberg@mit.edu

Education

Ph.D. in Biochemistry.            May 1995. University of Colorado at Boulder

                                                            Thesis advisor: Prof. M.H. Caruthers

 

B.S. in Chemistry.                    November 1989. University of Erlangen-Nürnberg,

                                                            Germany.

Experience

2002 -                                      Firmenich Associate Professor of Chemistry,

Massachusetts Institute of Technology.

1998 - 2002                             Assistant Professor of Chemistry

Massachusetts Institute of Technology.

1995 - 1997                             Research Fellow

                                                            Sloan-Kettering Institute for Cancer Research.

                                                            Mentor: Prof. S.J. Danishefsky

Awards

2002                                        Robert P. Goldberg Grand Prize (MIT 50K Competition) as

team member of ‘Ancora Pharmaceuticals’

2002                                        Harold E. Edgerton Faculty Achievement Award

2002                                        Alfred P. Sloan Research Scholar

2002                                        Glaxo-Smith-Kline Research Scholar Award

2000                                        CaP CURE Research Award

1999                                        CaP CURE Research Award

1999                                        Research Corporation “Research Innovation Award”

1999                                        Technology Review Top 100 Young Innovator Award

1999                                        Edgerly Science Partnership Fund Award

1999                                        Mizutani Foundation for Glycoscience Award

1998                                        CaP CURE Research Award

1997                                        Liebig Fellow

1990 - 1992                             Fulbright Scholar

1987 - 1992                             Bavarian Government Scholar

 

Visiting Professorship

1998                                        Rheinische-Wilhelms University Bonn, Germany

 

Named Lectures

2002                                Haynes-Morris Lecturer, University of Tennessee

2001                       Sigma-Xi Lecturer, MIT

 

Editorial Advisory Boards

2001-                                       Carbohydrate Research

2002-                                       Current Organic Synthesis

2002-                                       Mini Reviews in Organic Chemistry

 

Publications

(* denotes work done prior to present appointment)

 

*1.             Seeberger, P.H.; Yau, E.; Caruthers, M.H.; 2'-Deoxynucleoside-dithiophosphates:

            Synthesis and Biological Studies, J. Am. Chem. Soc. 1995, 117, 1472-1478.

 

*2.            Seeberger, P.H.; Caruthers, M.H.; Oxidative Formation of Phosphorodithioates

            via H-Phosphonodithioates, Tetrahedron  Lett. 1995, 36, 695-698.

 

*3.       Greef, C.H.; Seeberger, P.H.; Caruthers, M.H.; Beaton, G.; Bankaitis-Davis, D.;

            Synthesis of Phosphorodithioate RNA by the H-Phosphonothioate Method,

            Tetrahedron  Lett. 1996, 37, 4451-4454.

 

*4.            Seeberger, P.H.; Jorgensen, P.N.; Bankaitis-Davis, D.; Beaton, G.; Caruthers,

            M.H.; 5'-Dithiophosphoryl Deoxyoligonucleotides: Synthesis and Biological

            Studies, J. Am. Chem. Soc. 1996, 118, 9562-9566.

 

*5.            Seeberger, P.H.; Cirillo, P.F.; Hu, S.; Beebe, X., Bilodeau, M.T.; Danishefsky,

            S.J.; Synthesis of the ‘Core’ Pentasaccharide of N-linked Glycopeptides by the

            Glycal Assembly Method, Enantiomer 1996, 1, 311-323.

 

*6.            Seeberger, P.H.; Jordan, J.L.; Bankaitis-Davis, D.; Heil, J.; Munson, M.C.;

            Beaton, G.; Caruthers, M.H.; Solid-Phase Synthesis of Oligonucleotide- and

            Peptide-Dithiophosphates, in Innovation and Perspectives in Solid Phase Synthesis

            and Combinatorial Libraries (Epton, R.; Ed.), 1996, Mayflower, Birmingham,

            UK, 141-146.

 

*7.            Seeberger, P.H.; Beebe, X.; Sukenick, G.D.; Pochapsky, S.; Danishefsky, S.J.;

            Monitoring the Progress of Solid-Phase Oligosaccharide Synthesis by High-

            Resolution Magic Angle Spinning NMR: Observation of Enhanced Selectivity for

            b-Glycoside Formation from a-1,2-Anhydrosugar Donors in Solid Phase

            Couplings, Angew. Chem. 1997, 109, 507-509 and Angew. Chem. Int. Ed.

            1997, 36, 491-493.

 

*8.            Danishefsky, S.J.; Hu, S.; Cirillo, P.F.; Eckhardt, M.; Seeberger, P.H.; A

            Highly Convergent  Synthetic Route to Glycopeptides Carrying a High

            Mannose Core Pentasaccharide Domain N-linked to a Natural Peptide Motif,

            Chem. Eur. J. 1997, 3, 1617-1628.

 

*9.            Seeberger, P.H.; Eckhardt, M.; Gutteridge, C.A.; Danishefsky, S.J.; Coupling

            of Glycal Derived Thioethyl Glycosyl Donors with Glycal Acceptors. An Advance

            in the Scope of the Glycal Assembly, J. Am. Chem. Soc. 1997, 119, 10064-

            10072.

 

*10.            Seeberger, P.H.; Bilodeau, M.T.; Danishefsky, S.J.; Synthesis of Biologically

            Important Oligosaccharides and Other Glycoconjugates by the Glycal Assembly

            Method Aldrichchimica Acta 1997, 30, 75-92.

 

*11.     Zheng, C.; Seeberger, P.H.; Danishefsky, S.J.; Solid Support Oligosaccharide

            Synthesis: Construction of b-linked Oligosaccharides by Coupling of Glycal

            Derived Thioethyl Glycosyl Donors J. Org. Chem. 1998, 63, 1126-1130.

 

*12.             Seeberger, P.H., Caruthers, M.H.; Modified Oligonucleotides as Therapeutic

            Agents, in Applied Antisense Oligonucleotide Technology(Stein, C.; Krieg, A.M.

            Eds.), 1998, Wiley, New York, pp. 51.

 

*13.     Zheng, C.; Seeberger, P.H.; Danishefsky, S.J.; Amidoglycosylation of Polymer-

            bound Glycals: A Complete Synthesis of the Lewisb Blood Group Determinant

            Oligosaccharide Domain on a Solid Support Angew. Chem. 1998, 110, 831-834

            and Angew. Chem. Int. Ed. 1998, 37, 789-792.

 

*14.             Seeberger, P.H.; Danishefsky, S.J.; Solid Phase Synthesis of Oligosaccharides

            and Glycopeptides by the Glycal Assembly Method: A Five Year Retrospective

            Acc. Chem. Res. 1998, 31, 685-695.

 

*15.            Seeberger, P.H.; Zheng, C.; Danishefsky, S.J.; Solid-Phase Synthesis of

            Oligosaccharides via Glycal-derived Thioethyl Glycosyl Donors, in Innovation and

            Perspectives in Solid Phase Synthesis and Combinatorial Libraries (Epton, R.;

            Ed.), 1998, Mayflower, Birmingham, UK, 39-42.

 

*16.     Jenkins, K.E.; Higson, A.P.; Seeberger, P.H.; Caruthers, M.H.; Solid Phase

            Synthesis of O-Boranophosphopeptides and O-Dithiophosphopeptides, in

            Innovation and Perspectives in Solid Phase Synthesis and Combinatorial Libraries

            (Epton, R.; Ed.), 1998, Mayflower, Birmingham, UK, 225-228.

 

17.       Plante, O.J.; Seeberger, P.H. Anomeric Phosphorodithioates as Novel Glycosyl-

            ating Agents, J. Org. Chem. 1998, 63, 9150-9151.

 

*18.             Seeberger, P.H.; Bankaitis-Davis, D.; Beaton, G.; Caruthers, M.H.; Synthesis

            of Phosphorodithioate DNA by the H-Phosphonate Approach,Tetrahedron  1999,

            55, 5759-5772.

 

19.       Plante, O.J.; Andrade, R.B.; Seeberger, P.H. Synthesis and Use of Glycosyl

            Phosphates as Glycosylating Agents, Organic Letters 1999, 1, 211-214.

 

20.            Andrade, R.B.; Plante, O.J.; Melean, L.G.; Seeberger, P.H. Solid-Phase

            Oligosaccharide Synthesis:  Preparation of Complex Structures Using a Novel

            Linker and Different Glycosylating Agents, Organic Letters 1999, 1, 1811-1814.

 

21.            Seeberger, P.H., Roehrig, S., Schell, P.; Wang, Y.; Christ, W.J.; Selective

            Formation of C2 Azido Glucose Derivatives from Glucal Precursors Using the

            Azidonitration Reaction,Carbohydr. Res. 2000, 328, 61-69.

 

22.            Melean, L.G.; Haase, W.-C.; Seeberger, P.H.; A Novel 4,5-Dibromooctane-1,8-

            diol Linker for Solid-Phase Oligosaccharide Synthesis, Tetrahedron  Lett. 2000,

41, 4329-4333.

 

23.      Plante, O.J.; Buchwald, S.L.; Seeberger, P.H.; Halobenzyl Ethers as Protecting

Groups for Organic Synthesis, J. Am. Chem. Soc. 2000, 122, 7148-7149.

 

24.       Haase, W.-C.; Seeberger, P.H.;  Recent Progress in Polymer-Supported Synthesis

            of Oligosaccharides and Carbohydrate Libraries, Curr. Org. Chem. 2000, 4, 481-

            511.

 

25.            Seeberger, P.H.; Haase, W.-C.; Solid-Phase Oligosaccharide Synthesis and

            Combinatorial Carbohydrate Libraries, Chem. Rev. 2000,100, 4349-4394.

 

26.              Plante, O.J.; Palmacci, E.R.; Seeberger, P.H.; Formation of b-Glucoamines

and b-Mannose Linkages Using Glycosyl Phosphates; Organic Letters 2000, 2, 3841-3843.

 

27.       Love, K.R.; Seeberger, P.H.; Parachlorophenyl Carbonate as a Versatile Hydroxyl

Protecting Group; Synthesis 2001, 317-322.

 

28.       Plante, O.J.; Palmacci, E.R.; Seeberger, P.H.; Automated Solid-Phase Synthesis

of Oligosaccharides; Science 2001, 291, 1523-1527.

 

29.              Palmacci, E.R.; Seeberger, P.H.; The Synthesis of C- Aryl and C-Alkyl

Glycosides Using Glycosyl Phosphates; Organic Letters 2001, 3, 1547-1550.

 

30.             Seeberger P.H. Solid-Phase Oligosaccharide Synthesis. In: PG Wang, CR Bertozzi,

            Eds. Glycochemistry: Principles, Synthesis, and Applications. Marcel Dekker,

New York, 2001, 1-32.

 

31.              Wang, L.-X.; Melean, L.G.; Seeberger, P.H.; Walker, G.C.; Biotin Labeling

of the Symbiotically Important Succinoglycan Oligosaccharides of Rhizobium meliloti for Identification of Putative Plant Receptors, Carbohydr. Res. 2001, 333, 73-78.

 

32.              Hewitt, M.C.; Seeberger, P.H.; Solution and Solid Support Synthesis of a Potential Leishmaniasis Carbohydrate Vaccine;  J. Org. Chem. 2001, 66, 4233-4243.

 

33.              Schell, P.H.; Orgueira, H.A.; Roehrig, S.; Seeberger, P.H.; Synthesis and Transformations of D-Glucuronic and L-Iduronic Acid Glycals; Tetrahedron Lett. 2001, 42, 3811-3814.

 

34.              Yabe, T.; Shukla, D.; Spears, P.; Rosenberg, R.D.; Seeberger, P.H.; Shworak,

            N.;  A Portable Sulfotransferase Domain Determines Sequence Specificity of

            Heparan Sulfate 3-O-Sulfotransferases; Biochem. J. 2001, 359, 235-241.

 

35.              Plante, O.J.; Palmacci, E.R.; Andrade, R.B.; Seeberger, P.H.; Oligosaccharide Synthesis Using Glycosyl Phosphate and Dithiophosphate Triesters as Glycosylating Agents; J. Am. Chem. Soc. 2001, 123, 9545-9554.

 

36.              Seeberger, P.H.; Bartolozzi, A.; New Approaches to the Chemical Synthesis of Bioactive Oligosaccharides; Curr. Opin. Struct. Biol. 2001, 11, 587-592.

 

37.              Hewitt, M.C.; Seeberger P.H.; Automated Solid-Phase Synthesis of the Leishmania Cap Tetrasaccharide; Organic Letters 2001, 3, 3699-3702.

 

38.              Plante, O.J.; Palmacci, E.R.; Seeberger, P.H.; Development of an Automated Oligosaccharide Synthesizer; Adv. Carb. Chem Bioch. 2001, 58, in press.

 

39.              Palmacci, E.R.; Hewitt, M.C.; Seeberger P.H.; ‘Cap-Tag’ – Novel Methods for the Rapid Purification of Oligosaccharides Prepared by Automated Solid-Phase Synthesis; Angew. Chem. Int. Ed. 2001, 40, 4433-4437.

 

40.              Love, K.R.; Andrade, R.B.; Seeberger, P.H.; Linear Synthesis of a Protected H-type II Pentasaccharide Using Glycosyl Phosphate Building Blocks; J. Org. Chem. 2001, 66, 8165-8176.

 

41.              Palmacci, E.R.; Plante, O.J.; Seeberger, P.H.; Solution- and Solid-Phase Synthesis of Oligosaccharides Using Glycosyl Phosphates; Eur. J. Org. Chem. 2002, 595-606.

 

42.              Ratner, D.M.; Plante, O.J.; Seeberger, P.H.; A Linear Synthesis of Branched High-Mannose Oligosaccharides from the HIV-1 Viral Surface Envelope Glycoprotein gp120; Eur. J. Org. Chem. 2002, 826-833.

 

43.              Marcaurelle, L.A.; Seeberger, P.H.; Combinatorial Carbohydrate Chemistry; Curr. Opin. Chem. Bio. 2002, 6, 289-296.

 

44.              Jenkins, K.E.; Higson, A.P.; Seeberger, P.H.; Caruthers, M.H.; Solid-Phase Synthesis and Biochemical Studies of O-Boranophosphopeptides and O-Dithiophosphopeptides, J. Am. Chem. Soc. 2002, 124, 6584-6593.

 

45.              Orgueira, H.A.; Bartolozzi, A.; Schell, P.H.; Seeberger, P.H.; Stereocontrol of Glycosylation Reactions by Conformational Locking of the Glycosyl Acceptor in Disaccharide Formation; Angew. Chem. Int. Ed. 2002, 41, 2128-2131.

 

46.              Hunt, D.K.; Seeberger, P.H.; Linker Influence on the Stereochemical Outcome of Glycosylations Utilizing Solid Support-bound Glycosyl Phosphates; Organic Letters 2002, 4, 2751-2754.

 

47.              Schofield, L.; Hewitt, M.C.; Evans, K.; Siomos, M.A.; Seeberger, P.H.; Synthetic Glycosylphosphatidylinositol of Malaria as a Candidate Anti-toxic Vaccine; Nature, 2002, in press.

 

48.              Love, K.R.; Seeberger, P.H.; Carbohydrate Arrays and Biosensors as Tools for Glycomics; Angew. Chem. Int. Ed. 2002, 41, in press.

 

49.              Herzner, H.; Palmacci, E.R.; Seeberger, P.H.; A Short Total Synthesis of 8,10-O-Methylbergenin; Organic Letters 2002, 4, in press.

 

50.              Seeberger, P.H.; Automatisierte Festphasensynthese von Oligosacchariden; Nachr. Chem. 2002, in press.

 

51.              Melean, L.G.; Love, K.R.; Seeberger, P.H.; Toward the Automated Solid Phase Synthesis of Oligoglucosamines: Systematic Evaluation of Glycosyl Phosphate and Glycosyl Trichloroacetimidate Building Blocks; Carbohydr. Res. 2002, in press.

 

52.              Bosse, F.; Marcaurelle, L.A.; Seeberger, P.H.; Linear Synthesis of the Tumor-Associated Carbohydrate Antigens Globo-H, SSEA-3 and Gb3; J. Org. Chem. 2002, 66, in press.

 

53.              Botos, I.; O’Keefe, B.R.; Cartner, L.K.; Ratner, D.M.; Seeberger, P.H.; Boyd, M.R.; Wlodawer, A.; Structures of the Complexes of a Potent Anti-HIV Protein Cyanovirin-N and High-Mannose Saccharides, J. Biol. Chem. 2002, in press.

 

54.              Orgueira, H.A.; Bartolozzi, A.; Schell, P.H.; Litjens, R.; Palmacci, E.R.; Seeberger, P.H.; Modular Synthesis of Heparin Oligosaccharides Chem. Eur. J. 2002, in press.

 

55.              Love, K.R.; Seeberger, P.H.; Synthesis and Use of Glycosyl Phosphates as Glycosyl Donors; Organic Syntheses, submitted for publication.

Book Edited

 

1.         Solid Support Oligosaccharide Synthesis and Combinatorial Carbohydrate Libraries

            (Seeberger, P.H.; Ed.), Wiley-VCH, New York, 336pp, 2001.

 

Book Review

 

1.            Seeberger, P.H. “Bioorganic Chemistry: Carbohydrates.  Edited by S.M. Hecht”

            Carbohydrate Research 2000, 323,240-241.

 

Invited Lectures

 

1998

 

Eisai Research Institute, Andover, MA

Repligen Inc., Needham, MA

19th International Carbohydrate Symposium, San Diego, CA

Boston University School of Medicine

Novabiochem Inc. (Switzerland)

Boston Glycobiology Discussion Group

 

1999

 

Eberhard-Karls Universität Tuebingen (Germany)

217 th National ACS Meeting, Anaheim, CA

Ibis Pharmaceuticals, San Diego, CA

Carbohydrate Gordon Research Conference, Tilton, NH

Combinatorial Chemistry Gordon Research Conference, Tilton, NH

X th Eurocarb, Galway (Ireland)

ArQule Inc., Medford, MA

CaP CURE Research Conference, Lake Tahoe, NV

ACS Southeastern Regional Meeting, Knoxville, TN

Boston University, Dental School, Boston, MA

Sphinx Pharmaceuticals, Cambridge, MA

Harvard Medical School, Boston, MA

National Glycobiology Symposium, San Francisco, CA

Universität Karlsruhe (Germany)

 

2000

 

Universität Konstanz (Germany)

Bayer AG, Leverkusen, (Germany)

Johannes-Gutenberg Universität, Mainz (Germany)

Aventis Pharma, Frankfurt (Germany)

Aventis Crop Sciences, Frankfurt (Germany)

Ludwig-MaximiliansUniversität, Munich (Germany)

Organic Syntheses Symposium, MIT, Cambridge, MA

University of New Hampshire, Durham, NH

BASF, Worcester, MA

Merck, West Point, PA

City University New York, Hunter College, New York, NY

Sugen Inc., San Francisco, CA

Isis Pharmaceuticals, Carlsbad, CA

219 th National ACS Meeting, San Francisco

Biogen Inc., Cambridge, MA

National Cancer Institute, Frederick, MD

NSF “Frontiers in Glycoscience Workshop”, Arlington, VA

Carlsberg Laboratory, Copenhagen (Denmark)

Combinatorial Chemistry Gordon Research Conference, Il Ciocco, (Italy)

Ciba Specialty Chemicals, Grenzach (Germany)

Boehringer-Ingelheim, Biberach (Germany)

Merck KGaA, Darmstadt (Germany)

Bioorganic Gordon Research Conference, Andover, NH

ACS Northeastern Regional Meeting, Storrs, CT

Advances in Streamlined Synthesis Symposium, Boston University, Boston, MA

Whitehead Institute, Cambridge, MA

Proteoglycan Gordon Research Conference, Andover, NH

Boehringer-Ingelheim, Ridgefield, CT

Bayer AG, Leverkusen (Germany)

220th National ACS Meeting, Washington, DC

20th International Carbohydrate Symposium, Hamburg (Germany)

Brandeis University, Waltham, MA

CaP CURE Research Conference, Lake Tahoe, NV

Albany Molecular Research, Albany, NY

 

2001

 

California Institute of Technology, Pasadena, CA

National Cancer Institute, Frederick, MD

Ludwig-Maximilians Universität Munich  (Germany)

University of Chicago, Chicago, IL

Wayne State University, Detroit, MI

University of Utah, Salt Lake City, UT

Glycobiology Gordon Research Conference, Ventura, CA

Cotton Medal Symposium, Texas A&M University, College Station, TX

University of Illinois at Chicago, Chicago, IL

221st National ACS Meeting, San Diego, CA

Diversa Inc., San Diego, CA

SurfaceLogix Inc., Brighton, MA

NEOSE Technologies Inc., Horsham, PA

Eisai Research Institute, Andover, MA

Pfizer Inc., Groton, CT

Sigma Xi Lecture, Massachusetts Institute of Technology

Pharmacia Inc., Kalamazoo, MI

Lemieux Symposium, Chemical Institute of Canada, Montreal (Canada)

NSF “Physical Organic Chemistry Workshop”, Utica, IL

Caruthers Symposium, Boulder, CO

Alchemia Inc., Brisbane (Australia)

World Chemistry Congress, Brisbane (Australia)

Heterocycles Gordon Research Conference, Newport, RI

Ely Lilly, Indianapolis, IN

222nd National ACS Meeting, Chicago, IL

University of California, Berkeley, CA

CaP CURE Research Conference, Lake Tahoe, NV

University of Pennsylvania, Philadelphia, PA

Brown University, Providence, RI

Tufts University, Medford, MA

University of Rochester, Rochester, NY

45th Welch Foundation Conference, Houston, TX

DuPont Inc., Wilmington, DE

Swarthmore College, Swarthmore, PA

 

2002

 

University of Toronto, Toronto (Canada)

Haynes-Morris Lecture, University of Tennessee, Knoxville, TN

Cornell University, Ithaca, NY

New York University, New York City, NY

Eidgenoessisch Technische Hochschule (ETH), Zuerich (Switzerland)

Chemistry and Biology of Peptides Gordon Research Conference, Ventura, CA

 

University of Illinois, Urbana-Champaign, IL

Purdue University, West Lafayette, IN

Northwestern University, Evanston, IL

University of Texas, Southwestern Medical Center, Dallas, TX

University of Missouri St. Louis, MO

Washington University, St. Louis, MO

Schering-Plough, North Orange, NJ

North Jersey ACS Spring Symposium, Woodbridge, NJ

TechCon, DuPont Inc., Wilmington, DE

Bristol-Myers-Squibb, Princeton, NJ

21st International Carbohydrate Symposium, Cairns (Australia)

International GPI Anchor Symposium, Port Darwin (Australia)

14th International Conference on Organic Synthesis, Christchurch (New Zealand)

Victoria University, Wellington (New Zealand)

Massey University, Palmerston North (New Zealand)

 

Scheduled

 

224th National ACS Meeting, Boston, MA

CaP CURE Research Conference, Washington, DC

ACS Prospectives Conference “Combinatorial Chemistry”. Leesburg, VA

GlaxoSmithKline Research Conference, Research Triangle Park, NC

University of Connecticut, Storrs, CT

Yale University, New Haven, CT

Syracuse University, Syracuse, NY

Ohio State University, Columbus, OH

 

2003

 

XVII International Symposium on Glycoconjugates, Bangalore (India)

Case Western Reserve University, Cleveland, OH

LabAutomation 2003, Palm Springs, CA

Boston College, Chestnut Hill, MA

IUPAC/Canadian Society for Chemistry Meeting, Ottawa (Canada)

226th National ACS Meeting, New York, NY