Functional Groups in Biochemistry

Professor Serianni’s scientific research interests include methods development for site-specific isotopic labeling of carbohydrates and their derivatives, synthesis and conformational studies of simple and complex carbohydrates related to the N-glycans of human glycoproteins by nuclear magnetic resonance (NMR) spectroscopy, crystallography and other biophysical techniques, applications of molecular orbital theory and molecular dynamics to aid in the interpretation of NMR parameters in saccharides, and structure-function studies of non-enzymic protein glycation and chemical evolution. Professor Serianni has co-authored over 160 peer-reviewed research papers, and has been a recipient of the Horace S. Isbell Award (1988) from the Division of Carbohydrate Chemistry, American Chemical Society, and the Melville L. Wolfrom Award from the Division of Carbohydrate Chemistry, American Chemical Society (2006). He has also received the John Boezi Memorial Alumnus Award from Michigan State University (2001) and the Distinguished Alumnus Award from Albright College (1996). Prof. Serianni is an elected fellow of the American Association for the Advancement of Science (2010), a fellow of the American Chemical Society (2012), and a fellow of the Royal Society of Chemistry (2012). Prof. Serianni has served on multiple NIH and NSF grant review panels, and has served as an editor of Carbohydrate Research (an international journal in carbohydrate chemistry). He has taught multiple courses at the undergraduate and graduate levels ranging from advanced NMR spectroscopy to principles of sustainability. Professor Serianni co-founded Omicron Biochemicals, Inc. in 1982, a biotech company specializing in the synthesis of stable isotopically labeled carbohydrates, nucleosides and their derivatives. Omicron supplies >1000 non-GMP and cGMP products. The company has served as a critical resource for researchers in the glycoscience field.

Introduction and General Principles

1
(a) Hydroxyl R–OH
(b) Thiol R–SH

2
(a) Ether R1–O–R2
(b) Thioether R1–S–R2

3
(a) Disulfide R1–S–S–R2
(b) Peroxide R–O–O–H
R1–O–O–R2

4
(a) Carboxyl R–COOH
(b) Carboxyester R1–C(=O)–OR2
(c) Imidate R1–C(=NH)–OR2
(d) Thioester R1–C(=O)–SR2
(e) Phosphoester R1–O–PO3H2
R1–O–P(O2H)–R2
R1–O–P(O)(OR2)(OR3)
(f) Sulfoester R1–O–SO2OH
R1–O–SO2–O–R2

5
(a) Aldehyde R–CHO
(b) Carbonyl R1–C(=O)–R2
(c) Imine R–CH(=NH)
R1–C(=NH)–R2

6
(a) Ketoacid R–C(=O)–COOH
(b) Ketoacid R–C(=O)–CH2–COOH
R1–C(=O)–CHR2–COOH
R1–C(=O)–CR2R3–COOH

7
(a) Amine R1R2NH
R1R2R3N
R1R2R3R4N+
(b) Amide R–C(=O)–NH2
R1–C(=O)–NHR2
R1–C(=O)–NR1R2
(c) Amidine R1–C(=NH)–NH2

8
(a) Phosphoanhydride R–O–P(O)(OH)–O–P(O)(OH)2
R1–O–P(O)(OH)–O–P(O)(OH)–OR2
(b) Mixed Anhydride R–C(=O)–O–P(=O)O2H2
R1–C(=O)–O–P(=O)(OR2)(OH)

9
(a) Hemiacetal R1–O–CHR2–OH
(b) Acetal R1–O–CHR2–OR3
(c) Hemiketal R1–O–CR2R3–OH
(d) Ketal R1–O–CR2R3–OR4

Concluding Remarks
References