Manfred Hesse

Manfred Hesse studied Chemistry at the Humboldt University (East Berlin), at the Free University (West Berlin), and at the University of Zurich. He carried out his Ph.D. work under the guidance of Hans Schmid (1962). With the exception of a training period in mass spectrometry at F. Hoffmann-La Roche, Basel, he has been associated throughout his career with the Institute of Organic, first as Privatdozent (1966), then as Assistant Professor (1969) and in 1973 as Associate Professor. In 1983 he became Full Professor.

Research Interests:

The research interests of M. Hesse focused on the structure, biosynthesis, and synthesis of natural products, as well as mechanistic studies of ring enlargement reactions, and mass- spectral investigations of complex molecules. In the area of natural products, the biologically important polyamines, such as spermine and spermidine and their derivatives, are of special interest. Some of the derivatives are known as plant alkaloids, others were isolated from the venom of spiders and wasps, and belong to a new group of interesting neurotoxins. His goal in plant chemistry is concerned with the biogenesis of the spermine alkaloid aphelandrine from e.g. Aphelandra tetragona (Vahl) Nees., its function in the plant, as well as its synthesis. He is also interested in working out strategies for the synthesis of other macrocyclic polyamine alkaloids and polyamine toxins. The method of electrospray ionization mass spectrometry, which allows the determination of complex ionic structures from aqueous solutions, is of great help in analyzing these polar water-soluble polyamine derivatives. For some time, he has been investigating mechanistic aspects and synthetic uses of ring- enlargement reactions, such as the Zip-Reaction. This was discovered several years ago in M. Hesse's group. The transformation of cycloalkanones in to benzannelated lactams through imides has been achieved recently, and demonstrates the synthetic power of this rearrangement reaction.

Publications:

ELECTROSPRAY-IONIZATION MASS SPECTROMETRY.2. NEIGHBORING-GROUP PARTICIPATION IN THE MASS-SPECTRAL DECOMPOSITION OF 4-HYDROXYCINNAMOYL-SPERMIDINES

by W. Hu, E. Reder and M.Hesse  Helv. Chim. Acta 1996, 79, 2137-2151

ELECTROSPRAY-IONIZATION MASS SPECTROMETRY.
<3. ACID-CATALYZED ISOMERIZATION OF N,N'-BIS[(E)-3-(4-HYDROXYPHENYL)PROP-2-ENOYL]SPERMIDINES BY THE ZIP REACTION

by L. Bigler, C.F. Schnider, W. Hu and M. Hesse  Helv. Chim. Acta 1996, 79, 2152-2163

TOTAL SYNTHESIS OF (-)-(2R)-DIHYDROMYRICOIDINE

by U.A. Häusermann, A. Linden, J.G. Song and M. Hesse Helv. Chim. Acta 1996, 79, 1995-2003

ONCINOTINE-TYPE SPERMIDINE ALKALOIDS FROM ONCINOTIS TENUILOBA

by M.K.H. Doll, A. Guggisberg and M. Hesse
Helv. Chim. Acta 1996, 79, 973-981

TOTAL SYNTHESIS OF THE SPERMIDINE ALKALOID (+)-(9S,13S)-ISOCYCLOCELABENZINE

by K. Schultz and M. Hesse  Tetrahedron 1996, 52, 14189-14198

DETECTION OF NONCOVALENT COMPLEXES OF HYDROXAMIC-ACID DERIVATIVES BY MEANS OF ELECTROSPRAY MASS SPECTROMETRY

by L. Bigler, A. Baumeler, C. Werner and M. Hesse
Helv. Chim. Acta 1996, 79, 1701-1709

SYNTHESIS OF ONCINOTIN-11-ONE, A MACROCYCLIC POLYAMINE ALKALOID FROM ONCINOTIS TENUILOBA

by M.K.H. Doll, A. Guggisberg and M. Hesse
Helv. Chim. Acta 1996, 79, 1379-1386

ASYMMETRIC SYNTHESIS OF THE ALKALOIDS MAYFOLINE AND N(1)-ACETYL-N(1)-DEOXYMAYFOLINE

by P. Kuehne, A. Linden and M. Hesse
Helv. Chim. Acta 1996, 79, 1085-1094

STRUCTURE OF THE INTERMEDIATE OF A METHYLATION WITH (i-PrO)₂TiMe₂ - NMR INVESTIGATIONS AND CONFORMATIONAL ANALYSIS

by S. Hollenstein and M. Hesse
Helv. Chim. Acta 1996, 79, 827-836

REVERSED-PHASE HIGH-PERFORMANCE LIQUID CHROMATOGRAPHIC SEPARATION OF EPIMERIC ALKALOID N-OXIDES FROM THALICTRUM SIMPLEX L.

by M.P. Velcheva, C. Werner and M. Hesse
J. of Chromatography 1996, 730, 63-67

DEGRADATION OF THE POLYAMINE ALKALOID APHELANDRINE BY ENDOPHYTIC FUNGI ISOLATED FROM APHELANDRA TETRAGONA

by C. Werner, O. Petrini, and M. Hesse
FEMS Microbiol. Lett. 1997, 155(2), 147-153

A PUTRESCINE TRIAMIDE FROM LILIUM REGALE

by A. Linden, P. Kuehne, and M. Hesse
Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1997, C53(10), 1472-1475

ABSOLUTE CONFIGURATION OF MACROCYCLIC SPERMIDINE ALKALOIDS

by K. Schultz, P. Kuehne, U. A. Häusermann, and M. Hesse
Chirality 1997, 9(5/6), 523-528

SYNTHESES AND CHIROPTICAL PROPERTIES OF THE 13-MEMBERED SPERMIDINE ALKALOIDS (-)-(S)-CELACINNINE, (-)-(S)-CELABENZINE, (-)-(S)-CELAFURINE, AND (+)-(S)-VIBURNINE

by P. Kuehne, A. Guggisberg and M. Hesse
Helv. Chim. Acta 1997, 80(6), 1802-1808

THE TOTAL SYNTHESIS OF THE PAVINE ALKALOID THALIMONINE

by V.Pabuccuoglu and M. Hesse
Heterocycles 1997, 45(9), 1751-1758

SELECTIVE MONODERIVATIZATION OF PROPANE-1,3-DIAMINE WITH ACID CHLORIDES - HEXAHYDROPYRIMIDINE METHOD VS. STATISTIC METHOD

by C. Jentgens, S. Bienz and M. Hesse
Helv. Chim. Acta 1997, 80,1133-1143

SELECTIVE SYNTHESIS OF POLYAMINE DERIVATIVES: EFFICIENT DERIVATISATION OF THE SECONDARY AMINO GROUP OF N-MONOSUBSTITUTED 1,3-DIAMINES

by C. Jentgens, R. Hofmann, A. Guggisberg, S. Bienz and M. Hesse
Helv. Chim. Acta 1997, 80, 966-978

Synthesis of penta-N-protected homocaldopentamine and its selective acylation

by J. K. Pak, and M. Hesse
J. Org. Chem. 1998, 63(23), 8200-8204

Chiroptical properties of the protoverbine class of macrocyclic spermine alkaloids

by K. Drandarov, A. Guggisberg, A. Linden, and M. Hesse
Helv. Chim. Acta 1998, 81(10), 1773-1791

Amaryllidaceae alkaloids: (+)-tazettine, (+)-3-O-demethylcriwelline and (+)-3-epimacronine at 173 K

by A. Linden, G. Akineri, S. Noyan, T. Gozler, and M. Hesse
Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1998, C54(11), 1653-1659

The gracilines: a novel subgroup of the Amaryllidaceae alkaloids

by S. Noyan, G. H. Rentsch, M. A.  Onur, T. Gozler, B. Gozler, and M. Hesse
Heterocycles 1998, 48(9), 1777-1791

Online coupling of high-performance liquid chromatography to atmospheric pressure chemical ionization mass spectrometry (HPLC/APCI-MS and MS/MS). The pollen analysis of Hippeastrum hortorum

by N. Youhnovsky, L. Bigler, C. Werner, and M. Hesse
Helv. Chim. Acta 1998, 81(9), 1654-1671

A novel NO₂/OH exchange in a-nitro ketones. A mechanistic investigation

by A. Yurdakul, C. Gurtner, E.-S. Jung, A. Lorenzi-Riatsch, A. Linden, A. Guggisberg, S. Bienz, and M. Hesse
Helv. Chim. Acta 1998, 81(8), 1373-1392

Synthesis of penta-N-protected thermopentamine and its selective deprotection

by J. K. Pak, A. Guggisberg, and M. Hesse
Tetrahedron 1998, 54(28), 8035-8046

Polyamines and polyamine derivatives in the nature.
As manifold the functions of polyamines are in human, animals and plants, as manifold are their potential applications. In cancer therapy, as a tool in neurochemistry or as natural pesticide

by H. Geneste and M. Hesse
Chem. Unserer Zeit 1998, 32(4), 206-218

Synthesis of the spermidine alkaloid (-)-(4R)-dihydroisomyricoidine

by A. Horni, A. Linden, and M. Hesse
Helv. Chim. Acta 1998, 81(7), 1303-1318

The photoisomerization behavior of the (4-hydroxycinnamoyl)spermidines

by W. Hu and M. Hesse
Helv. Chim. Acta 1998, 81(2), 342-352

Total syntheses of natural occurring spermidine alkaloids: (+)-(2S)-dihydromyricoidine and (+)-(2S)-myricoidine<

by U. A. Häusermann and M. Hesse
Tetrahedron Lett. 1998, 39(3/4), 257-260

Natural polyamine derivatives - new aspects of their isolation, structure elucidation, and synthesis

by A. Guggisberg and M. Hesse
Alkaloids (Academic Press) 1998, 50, 219-256