Wikipedia

Anthony Serianni

Anthony Stephen Serianni (born November 18, 1953) is an American biochemist, academic, and author. He is the president and CEO of Omicron Biochemicals[1] as well as a professor of Chemistry and Biochemistry at the University of Notre Dame.[2]

Anthony Stephen Serianni
Born (1953-11-18) November 18, 1953 (age 70)
NationalityAmerican
EducationBS., Biochemistry
PhD., Biochemistry
Postdoctoral research., Biochemistry, Molecular and Cell Biology
Alma materAlbright College
Michigan State University
Cornell University
Occupation(s)Biochemist, academic and author
Scientific career
InstitutionsUniversity of Notre Dame
Omicron Biochemicals

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),[3] University of Notre Dame's Kaneb Teaching Award (2003),[4] and American Chemical Society's Melville L. Wolfrom Award in Carbohydrate Chemistry (2006).[5]

Serianni is an elected Fellow of the Royal Society of Chemistry,[6] American Chemical Society,[7] and the American Association for the Advancement of Science.[8]

Education

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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.[2]

Career

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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.[2]

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.[9]

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

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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.[10]

Synthesis of labeled saccharides

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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.[11]

NMR methods for saccharide structure and reactivity

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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.[12] 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.[13] This work showed that furanose ring anomeric configuration influences ring-opening rates via anchimeric assistance.[14] In addition, his studies of phosphorylated sugars highlighted the role of intramolecular catalysis by phosphate in anomerization.[15]

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.[16] 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.[17]

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.[18]

NMR spin-couplings for saccharide structure

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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 1JCC in saccharides, highlighting the effectiveness of combining NMR studies with stable isotopes and ab initio molecular orbital calculations.[19] His contributions also include using 1JCH values as conformational probes for furanose rings[20] and establishing the first 3JCOCC Karplus curve for O-glycosidic linkages, illustrating the influence of terminal electronegative substituents on coupling magnitude.[21][22] Additionally, he explored the correlation of J-couplings with exocyclic hydroxymethyl group conformations, the dependence of 2JCCH values on C–O bond rotations, and the measurement of hydrogen bond strengths via 1JCH.[23][24] 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.[25]

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.[26] 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.[27] 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.[28]

Awards and honors

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  • 2001 – John A. Boezi Memorial Alumnus Award, Michigan State University[3]
  • 2003 – Kaneb Teaching Award, University of Notre Dame[4]
  • 2006 – Melville L. Wolfrom Award in Carbohydrate Chemistry, American Chemical Society[5]
  • 2010 – Elected Fellow, American Association for the Advancement of Science[8]
  • 2012 – Elected Fellow, American Chemical Society[7]
  • 2012 – Elected Fellow, Royal Society of Chemistry[6]

Bibliography

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Books

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

Selected articles

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  • 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 2JHH, 3JHH, and 1JCH 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.

References

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  1. ^ "Omicron Biochemicals–Presiden's Note".
  2. ^ a b c "University of Notre Dame–Anthony Serianni".
  3. ^ a b "Dr. Anthony Serianni".
  4. ^ a b "Joyce Award and Kaneb Award Recipients Cumulative 1999 to 2023" (PDF).
  5. ^ a b "The Melville L. Wolfrom Award".
  6. ^ a b "Dovichi and Serianni named Fellows of the Royal Chemistry Society".
  7. ^ a b "ACS Fellow Award".
  8. ^ a b "AAAS–Elected Fellows".
  9. ^ "Lake Papakeechie Sustainability Initiative".
  10. ^ "Saccharide antifreeze compositions".
  11. ^ Hayes, Michael L.; Pennings, Nicholas J.; Serianni, Anthony S.; Barker, Robert (1982). "Epimerization of aldoses by molybdate involving a novel rearrangement of the carbon skeleton". Journal of the American Chemical Society. 104 (24): 6764–6769. doi:10.1021/ja00388a047.
  12. ^ Serianni, Anthony S.; Nunez, Hernan A.; Barker, Robert (1979). "Carbon-13-enriched carbohydrates. Preparation of aldononitriles and their reduction with a palladium catalyst". Carbohydrate Research. 72: 71–78. doi:10.1016/S0008-6215(00)83924-5.
  13. ^ Serianni, Anthony S.; Pierce, John; Huang, Shaw Guang; Barker, Robert (1982). "Anomerization of furanose sugars: kinetics of ring-opening reactions by proton and carbon-13 saturation-transfer NMR spectroscopy". Journal of the American Chemical Society. 104 (15): 4037–4044. doi:10.1021/ja00379a001.
  14. ^ Snyder, Joseph R.; Johnston, Eric R.; Serianni, Anthony S. (1989). "D-Talose anomerization: NMR methods to evaluate the reaction kinetics". Journal of the American Chemical Society. 111 (7): 2681–2687. doi:10.1021/ja00189a050.
  15. ^ Pierce, John; Serianni, Anthony S.; Barker, Robert (1985). "Anomerization of furanose sugars and sugar phosphates". Journal of the American Chemical Society. 107 (8): 2448–2456. doi:10.1021/ja00294a041.
  16. ^ Kukal, Olga; Serianni, Anthony S.; Duman, John G. (1988). "Glycerol metabolism in a freeze-tolerant arctic insect: an in vivo13C NMR study". Journal of Comparative Physiology B. 158 (2): 175–183. doi:10.1007/BF01075831. PMID 3170824.
  17. ^ Kukal, Olga; Duman, John G.; Serianni, Anthony S. (1989). "Cold-induced mitochondrial degradation and cryoprotectant synthesis in freeze-tolerant arctic caterpillars". Journal of Comparative Physiology B. 158 (6): 661–671. doi:10.1007/BF00693004. PMID 2715455.
  18. ^ Serianni, Anthony S.; Chipman, Daniel M. (1987). "Furanose ring conformation: the application of ab initio molecular orbital calculations to the structure and dynamics of erythrofuranose and threofuranose rings". Journal of the American Chemical Society. 109 (18): 5297–5303. doi:10.1021/ja00252a001.
  19. ^ Carmichael, Ian; Chipman, Daniel M.; Podlasek, Carol A.; Serianni, Anthony S. (1993). "Torsional effects on the one-bond 13C-13C spin coupling constant in ethylene glycol: insights into the behavior of 1JCC in carbohydrates". Journal of the American Chemical Society. 115 (23): 10863–10870. doi:10.1021/ja00076a050.
  20. ^ Serianni, Anthony S.; Wu, Jian; Carmichael, Ian (1995). "One-bond 13C-1H spin-coupling constants in aldofuranosyl rings: effect of conformation on coupling magnitude". Journal of the American Chemical Society. 117 (33): 8645–8650. doi:10.1021/ja00138a021.
  21. ^ Bose, Bidisha; Zhao, Shikai; Stenutz, Roland; Cloran, Francis; Bondo, Paul B.; Bondo, Gail; Hertz, Brian; Carmichael, Ian; Serianni, Anthony S. (1998). "Three-Bond C−O−C−C Spin-Coupling Constants in Carbohydrates: Development of a Karplus Relationship". Journal of the American Chemical Society. 120 (43): 11158–11173. doi:10.1021/ja981127f.
  22. ^ Zhao, Hongqiu; Carmichael, Ian; Serianni, Anthony S. (2008). "Oligosaccharide Trans-Glycoside 3JCOCC Karplus Curves Are Not Equivalent: Effect of Internal Electronegative Substituents". The Journal of Organic Chemistry. 73 (8): 3255–3257. doi:10.1021/jo702288h. PMID 18351773.
  23. ^ Thibaudeau, Christophe; Stenutz, Roland; Hertz, Brian; Klepach, Thomas; Zhao, Shikai; Wu, Qingquan; Carmichael, Ian; Serianni, Anthony S. (2004). "Correlated C−C and C−O Bond Conformations in Saccharide Hydroxymethyl Groups: Parametrization and Application of Redundant 1H−1H, 13C−1H, and 13C−13C NMR J-Couplings". Journal of the American Chemical Society. 126 (48): 15668–15685. doi:10.1021/ja0306718. PMID 15571389.
  24. ^ Maiti, Nakul C.; Zhu, Yuping; Carmichael, Ian; Serianni, Anthony S.; Anderson, Vernon E. (2006). "1JCH Correlates with Alcohol Hydrogen Bond Strength". The Journal of Organic Chemistry. 71 (7): 2878–2880. doi:10.1021/jo052389k. PMID 16555846.
  25. ^ Klepach, Thomas E.; Carmichael, Ian; Serianni, Anthony S. (2005). "Geminal 2JCCH Spin−Spin Coupling Constants as Probes of the φ Glycosidic Torsion Angle in Oligosaccharides". Journal of the American Chemical Society. 127 (27): 9781–9793. doi:10.1021/ja040251y. PMID 15998083.
  26. ^ Walters, Kent R.; Serianni, Anthony S.; Sformo, Todd; Barnes, Brian M.; Duman, John G. (2009). "A nonprotein thermal hysteresis-producing xylomannan antifreeze in the freeze-tolerant Alaskan beetle Upis ceramboides". Proceedings of the National Academy of Sciences. 106 (48): 20210–20215. Bibcode:2009PNAS..10620210W. doi:10.1073/pnas.0909872106. PMC 2787118. PMID 19934038.
  27. ^ Zhang, Wenhui; Carmichael, Ian; Serianni, Anthony S. (2011). "Rearrangement of 3-Deoxy-d-erythro-hexos-2-ulose in Aqueous Solution: NMR Evidence of Intramolecular 1,2-Hydrogen Transfer". The Journal of Organic Chemistry. 76 (20): 8151–8158. doi:10.1021/jo200288t. PMID 21793547.
  28. ^ Zhang, Wenhui; Serianni, Anthony S. (2012). "Phosphate-Catalyzed Degradation of d-Glucosone in Aqueous Solution Is Accompanied by C1–C2 Transposition". Journal of the American Chemical Society. 134 (28): 11511–11524. doi:10.1021/ja3020296. PMID 22650268.
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