Anthony Serianni

Anthony Stephen Serianni
Born	(1953-11-18) November 18, 1953
Nationality	American
Education	BS., Biochemistry PhD., Biochemistry Postdoctoral research., Biochemistry, Molecular and Cell Biology
Alma mater	Albright College Michigan State University Cornell University
Occupation(s)	Biochemist, academic and author
Scientific career
Institutions	University of Notre Dame Omicron Biochemicals

Anthony Stephen Serianni (born November 18, 1953) is an American biochemist, academic, and author. He is the president and CEO of Omicron Biochemicals as well as a professor of Chemistry and Biochemistry at the University of Notre Dame.

Serianni's publications include journal articles and two books, with his research focusing on catalysis in chemical and enzymatic systems, carbohydrate and nucleoside chemistry, biomolecular dynamics using NMR and computational methods, isotope labeling in biologically important compounds, and NMR-based studies of reaction mechanisms. He has received Michigan State University's John A. Boezi Memorial Alumnus Award (2001), University of Notre Dame's Kaneb Teaching Award (2003), and American Chemical Society's Melville L. Wolfrom Award in Carbohydrate Chemistry (2006).

Serianni is an elected Fellow of the Royal Society of Chemistry, American Chemical Society, and the American Association for the Advancement of Science.

Education

Serianni graduated with a BS in biochemistry from Albright College in 1975, then earned his PhD from Michigan State University in 1980 while working as a Graduate Research Assistant from 1975 to 1979. Following his doctoral studies, he served as a Postdoctoral Research Associate in the Section of Biochemistry at Cornell University from 1980 to 1982.

Career

In 1982, Serianni co-founded Omicron Biochemicals, and he has held the position of president and CEO since then. Concurrently, he continued his academic career at the University of Notre Dame, initially as an assistant professor, later advancing to associate professor, and has been a professor of chemistry and biochemistry since 1999.

Serianni founded the Lake Papakeechie Sustainability Initiative (LaPSI) in 2011, which focused on preserving the health of the Wawasee Area watershed in Indiana. Through Omicron Biochemicals, he supported LaPSI in establishing a laboratory at the Papakeechie Protective Association (PPA) headquarters in Syracuse, Indiana.

Serianni has held leadership roles within the American Chemical Society, serving as secretary, chairman-elect, chairman, past-chairman, and councilor of the Division of Carbohydrate Chemistry.

Research

Serianni has contributed to the fields of chemistry, biochemistry, and biomedicine by studying the structural and dynamic properties of saccharides, their reactivity, and their role in biological processes, particularly concerning metabolic pathways and disease mechanisms. He holds a patent for elucidating the structure of a novel non-protein thermal hysteresis compound based on a xylo-mannan oligosaccharide scaffold.

Synthesis of labeled saccharides

During his graduate studies at Michigan State University under Robert Barker, Serianni focused on synthesizing stable isotopically labeled saccharides, primarily using ¹³C, for structural, dynamic, and reactivity studies via NMR. To address the limited development of labeled saccharides, he introduced a chemical method for site-specific incorporation of ¹³C and other stable isotopes into aldoses through cyanohydrin reduction, bypassing the traditional Kiliani-Fischer synthesis. He also demonstrated the use of enzymes to convert labeled aldoses into valuable ketoses and oligosaccharides, and discovered a new mechanism of saccharide backbone rearrangement (C1–C2 transposition) catalyzed by molybdate ion.

NMR methods for saccharide structure and reactivity

Serianni's research on NMR methods centered on the NMR-based kinetic measurements of saccharide anomerization, the use of stable isotopes to study in vivo biological metabolism; and the application of ab initio molecular orbital calculations to saccharide structure and conformation. He showed that saturation-transfer NMR methods could measure unidirectional rate constants for aldose anomerization by selectively saturating the acyclic form, which allowed for precise determination of ring-opening and ring-closing rate constants. This work showed that furanose ring anomeric configuration influences ring-opening rates via anchimeric assistance. In addition, his studies of phosphorylated sugars highlighted the role of intramolecular catalysis by phosphate in anomerization.

In collaboration with John Duman, Serianni developed isotope-based NMR tools to study sugar metabolism in the freeze-tolerant organism Gynophora groenlandica. His lab designed a 16-mm ¹³C NMR probe for live larvae injected with labeled saccharides, allowing real-time, non-invasive monitoring. To complement these in vivo studies, he conducted in vitro experiments, incubating specific larvae organs with labeled sugars to map metabolic pathways, revealing metabolic triggers for polyol production, such as glycerol, and explored the effects of hypoxia, mitochondrial changes, and cryoprotectant production.

Another line of investigation in Serianni's early lab focused on applying ab initio molecular orbital (MO) theory to study saccharide structure and conformation. In 1987, he collaborated with Daniel Chipman to publish a study using the STO-3G level of ab initio MO calculations to examine the tetrofuranose ring system.

NMR spin-couplings for saccharide structure

Serianni has worked on developing NMR spin-couplings as quantitative probes of saccharide structure and conformation in solution, publishing over 50 papers on carbon-based J-couplings with Ian Carmichael. His work, initiated in 1993 with a publication in JACS, showcased a Karplus-like relationship for ¹J_CC in saccharides, highlighting the effectiveness of combining NMR studies with stable isotopes and ab initio molecular orbital calculations. His contributions also include using ¹J_CH values as conformational probes for furanose rings and establishing the first ³J_COCC Karplus curve for O-glycosidic linkages, illustrating the influence of terminal electronegative substituents on coupling magnitude. Additionally, he explored the correlation of J-couplings with exocyclic hydroxymethyl group conformations, the dependence of ²J_CCH values on C–O bond rotations, and the measurement of hydrogen bond strengths via ¹J_CH. He introduced a mathematical treatment of J-coupling ensembles (MA'AT analysis) to calculate phi and psi population distributions in O-glycosidic linkages, enabling experimental validation of molecular dynamics predictions.

With his group, Serianni has analyzed the mechanisms of saccharide degradation using stable isotopes and NMR. In 2011, he demonstrated that the dicarbonyl sugar 3-deoxyglucosone (3DG) degrades in aqueous solution via a 1,2-hydrogen transfer mechanism, resulting in C2-epimeric metasaccharinic acids. Building upon earlier work, he examined the effect of pyridoxamine on 3DG degradation as high glucose concentrations in the blood can lead to the in vivo production of 3DG, causing cellular damage through protein glycation and other harmful reactions. Subsequently, in 2012, his group discovered an unexpected rearrangement of D-glucosone, wherein the molecule undergoes C1–C2 transposition during its conversion to D-ribulose.

Awards and honors

• 2001 – John A. Boezi Memorial Alumnus Award, Michigan State University
• 2003 – Kaneb Teaching Award, University of Notre Dame
• 2006 – Melville L. Wolfrom Award in Carbohydrate Chemistry, American Chemical Society
• 2010 – Elected Fellow, American Association for the Advancement of Science
• 2012 – Elected Fellow, American Chemical Society
• 2012 – Elected Fellow, Royal Society of Chemistry

Bibliography

Books

• ¹³C Nuclear Magnetic Resonance Spectra of the Monosaccharides: Natural and Stable Isotopically-Enriched Compounds (1986)
• NMR Applications in Biopolymers (1990)

Selected articles

• Hayes, M. L., Pennings, N. J., Serianni, A. S., & Barker, R. (1982). Epimerization of aldoses by molybdate involving a novel rearrangement of the carbon skeleton. Journal of the American Chemical Society, 104(24), 6764–6769.
• Podlasek, C. A., Wu, J., Stripe, W. A., Bondo, P. B., & Serianni, A. S. (1995). [¹³C] Enriched methyl aldopyranosides: Structural interpretations of 13C-1H spin-coupling constants and 1H chemical shifts. Journal of the American Chemical Society, 117(33), 8635–8644.
• Zhu, Y., Zajicek, J., & Serianni, A. S. (2001). Acyclic forms of [1-¹³C] aldohexoses in aqueous solution: Quantitation by ¹³C NMR and deuterium isotope effects on tautomeric equilibria. The Journal of Organic Chemistry, 66(19), 6244–6251.
• Stenutz, R., Carmichael, I., Widmalm, G., & Serianni, A. S. (2002). Hydroxymethyl group conformation in saccharides: Structural dependencies of ²J_HH, ³J_HH, and ¹J_CH spin−spin coupling constants. The Journal of Organic Chemistry, 67(3), 949–958.
• Voziyan, P. A., Khalifah, R. G., Thibaudeau, C., Yildiz, A., Jacob, J., Serianni, A. S., & Hudson, B. G. (2003). Modification of proteins in vitro by physiological levels of glucose: Pyridoxamine inhibits conversion of Amadori intermediate to advanced glycation end-products through binding of redox metal ions. Journal of Biological Chemistry, 278(47), 46616–46624.
• Zhang, W., Meredith, R. J., Wang, X., Woods, R. J., Carmichael, I., & Serianni, A. S. (2024). Does Inter-Residue Hydrogen Bonding in β-(1→4)-Linked Disaccharides Influence Linkage Conformation in Aqueous Solution? The Journal of Physical Chemistry B, 128(10), 2317–2325.