Norman Oppenheimer, PhD

Professor

Department of Pharmaceutical Chemistry

[email protected]

Phone: +1 415 476-3038

Fax: +1 415 476-0688

513 Parnassus Ave, MSB, Rm 1124A

UCSF Box 0912

San Francisco, CA 94117

United States

Links

UCSF Profiles

Educational programs

PharmD Degree Program

What I do

Since retiring, I continue to teach PC 131 and lecture in PC 122.

Research keywords

Adenosine Diphosphate Ribose, ADP-ribosyl Cyclase, NAD, Aldehydes, Alcohol Dehydrogenase

Publications

Malver O, Sebastian MJ, Oppenheimer NJ. Alteration in substrate specificity of horse liver alcohol dehydrogenase by an acyclic nicotinamide analog of NAD(+). DNA Repair (Amst). 2014 Nov; 23:95-100.

Egea PF, Muller-Steffner H, Kuhn I, Cakir-Kiefer C, Oppenheimer NJ, Stroud RM, Kellenberger E, Schuber F. Insights into the mechanism of bovine CD38/NAD+glycohydrolase from the X-ray structures of its Michaelis complex and covalently-trapped intermediates. PLoS One. 2012; 7(4):e34918.

Graeff R, Liu Q, Kriksunov IA, Kotaka M, Oppenheimer N, Hao Q, Lee HC. Mechanism of cyclizing NAD to cyclic ADP-ribose by ADP-ribosyl cyclase and CD38. J Biol Chem. 2009 Oct 02; 284(40):27629-36.

Liu Q, Graeff R, Kriksunov IA, Jiang H, Zhang B, Oppenheimer N, Lin H, Potter BV, Lee HC, Hao Q. Structural basis for enzymatic evolution from a dedicated ADP-ribosyl cyclase to a multifunctional NAD hydrolase. J Biol Chem. 2009 Oct 02; 284(40):27637-45.

Lund FE, Muller-Steffner H, Romero-Ramirez H, Moreno-García ME, Partida-Sánchez S, Makris M, Oppenheimer NJ, Santos-Argumedo L, Schuber F. CD38 induces apoptosis of a murine pro-B leukemic cell line by a tyrosine kinase-dependent but ADP-ribosyl cyclase- and NAD glycohydrolase-independent mechanism. Int Immunol. 2006 Jul; 18(7):1029-42.

Gasser A, Glassmeier G, Fliegert R, Langhorst MF, Meinke S, Hein D, Krüger S, Weber K, Heiner I, Oppenheimer N, Schwarz JR, Guse AH. Activation of T cell calcium influx by the second messenger ADP-ribose. J Biol Chem. 2006 Feb 03; 281(5):2489-96.

Krebs C, Adriouch S, Braasch F, Koestner W, Leiter EH, Seman M, Lund FE, Oppenheimer N, Haag F, Koch-Nolte F. CD38 controls ADP-ribosyltransferase-2-catalyzed ADP-ribosylation of T cell surface proteins. J Immunol. 2005 Mar 15; 174(6):3298-305.

Gerth A, Nieber K, Oppenheimer NJ, Hauschildt S. Extracellular NAD+ regulates intracellular free calcium concentration in human monocytes. Biochem J. 2004 Sep 15; 382(Pt 3):849-56.

Moreno-García ME, Partida-Sánchez S, Primack J, Sumoza-Toledo A, Muller-Steffner H, Schuber F, Oppenheimer N, Lund FE, Santos-Argumedo L. CD38 is expressed as noncovalently associated homodimers on the surface of murine B lymphocytes. Eur J Biochem. 2004 Mar; 271(5):1025-34.

Partida-Sánchez S, Goodrich S, Kusser K, Oppenheimer N, Randall TD, Lund FE. Regulation of dendritic cell trafficking by the ADP-ribosyl cyclase CD38: impact on the development of humoral immunity. Immunity. 2004 Mar; 20(3):279-91.

Partida-Sánchez S, Iribarren P, Moreno-García ME, Gao JL, Murphy PM, Oppenheimer N, Wang JM, Lund FE. Chemotaxis and calcium responses of phagocytes to formyl peptide receptor ligands is differentially regulated by cyclic ADP ribose. J Immunol. 2004 Feb 01; 172(3):1896-906.

Lacapère JJ, Boulla G, Lund FE, Primack J, Oppenheimer N, Schuber F, Deterre P. Fluorometric studies of ligand-induced conformational changes of CD38. Biochim Biophys Acta. 2003 Nov 03; 1652(1):17-26.

Jackson MD, Schmidt MT, Oppenheimer NJ, Denu JM. Mechanism of nicotinamide inhibition and transglycosidation by Sir2 histone/protein deacetylases. J Biol Chem. 2003 Dec 19; 278(51):50985-98.

Guse AH, Cakir-Kiefer C, Fukuoka M, Shuto S, Weber K, Bailey VC, Matsuda A, Mayr GW, Oppenheimer N, Schuber F, Potter BV. Novel hydrolysis-resistant analogues of cyclic ADP-ribose: modification of the "northern" ribose and calcium release activity. Biochemistry. 2002 May 28; 41(21):6744-51.

Partida-Sánchez S, Cockayne DA, Monard S, Jacobson EL, Oppenheimer N, Garvy B, Kusser K, Goodrich S, Howard M, Harmsen A, Randall TD, Lund FE. Cyclic ADP-ribose production by CD38 regulates intracellular calcium release, extracellular calcium influx and chemotaxis in neutrophils and is required for bacterial clearance in vivo. Nat Med. 2001 Nov; 7(11):1209-16.

Cakir-Kiefer C, Muller-Steffner H, Oppenheimer N, Schuber F. Kinetic competence of the cADP-ribose-CD38 complex as an intermediate in the CD38/NAD+ glycohydrolase-catalysed reactions: implication for CD38 signalling. Biochem J. 2001 Sep 01; 358(Pt 2):399-406.

Buckley N, Oppenheimer NJ. Reactions of Charged Substrates. 8. The Nucleophilic Substitution Reactions of (4-Methoxybenzyl)dimethylsulfonium Chloride. J Org Chem. 1997 Feb 07; 62(3):540-551.

Oppenheimer NJ, Henehan GT, Huete-Pérez JA, Ito K. P. putida formaldehyde dehydrogenase. An alcohol dehydrogenase masquerading as an aldehyde dehydrogenase. Adv Exp Med Biol. 1997; 414:417-23.

Buckley N, Oppenheimer NJ. Reactions of Charged Substrates. 6. The Methoxymethyl Carbenium Ion Problem. 1. A Semiempirical Study of the Kinetic and Thermodynamic Stabilities of Linear and Cyclic Oxo- and Thiocarbenium Ions Generated from Pyridinium and Dimethylanilinium Ions. J Org Chem. 1996 Nov 15; 61(23):8039-8047.

Buckley N, Oppenheimer NJ. Reactions of Charged Substrates. 7. The Methoxymethyl Carbenium Ion Problem. 2. A Semiempirical Study of the Kinetic and Thermodynamic Stabilities of Linear and Cyclic Oxo- and Thiocarbenium Ions Generated from Aldehyde Hydrates, Hemiacetals, Acetals, and Methyl Ribosides and Glucosides. J Org Chem. 1996 Nov 15; 61(23):8048-8062.

Buckley N, Oppenheimer NJ. Reactions of Charged Substrates. 5. The Solvolysis and Sodium Azide Substitution Reactions of Benzylpyridinium Ions in Deuterium Oxide. J Org Chem. 1996 Oct 18; 61(21):7360-7372.

Buckley N, Maltby D, Burlingame AL, Oppenheimer NJ. Reactions of Charged Substrates. 4. The Gas-Phase Dissociation of (4-Substituted benzyl)dimethylsulfoniums and -pyridiniums. J Org Chem. 1996 Apr 19; 61(8):2753-2762.

Henehan GT, Chang SH, Oppenheimer NJ. Aldehyde dehydrogenase activity of Drosophila melanogaster alcohol dehydrogenase: burst kinetics at high pH and aldehyde dismutase activity at physiological pH. Biochemistry. 1995 Sep 26; 34(38):12294-301.

Oppenheimer NJ, Henehan GT. Horse liver alcohol dehydrogenase-catalyzed aldehyde oxidation. The sequential oxidation of alcohols to carboxylic acids under NADH recycling conditions. Adv Exp Med Biol. 1995; 372:407-15.

Muller-Steffner H, Muzard M, Oppenheimer N, Schuber F. Mechanistic implications of cyclic ADP-ribose hydrolysis and methanolysis catalyzed by calf spleen NAD+glycohydrolase. Biochem Biophys Res Commun. 1994 Nov 15; 204(3):1279-85.

Oppenheimer NJ. NAD hydrolysis: chemical and enzymatic mechanisms. Mol Cell Biochem. 1994 Sep; 138(1-2):245-51.

Henehan GT, Oppenheimer NJ. Horse liver alcohol dehydrogenase-catalyzed oxidation of aldehydes: dismutation precedes net production of reduced nicotinamide adenine dinucleotide. Biochemistry. 1993 Jan 26; 32(3):735-8.

Henehan GT, Kenyon GL, Oppenheimer NJ. The oxidation of aldehydes by horse liver alcohol dehydrogenase. Adv Exp Med Biol. 1993; 328:481-91.

McDonald LJ, Wainschel LA, Oppenheimer NJ, Moss J. Amino acid-specific ADP-ribosylation: structural characterization and chemical differentiation of ADP-ribose-cysteine adducts formed nonenzymatically and in a pertussis toxin-catalyzed reaction. Biochemistry. 1992 Dec 01; 31(47):11881-7.

Muller-Steffner HM, Malver O, Hosie L, Oppenheimer NJ, Schuber F. Slow-binding inhibition of NAD+ glycohydrolase by arabino analogues of beta-NAD. J Biol Chem. 1992 May 15; 267(14):9606-11.

Handlon AL, Oppenheimer NJ. Thiol reduction of 3'-azidothymidine to 3'-aminothymidine: kinetics and biomedical implications. Pharm Res. 1988 May; 5(5):297-9.

Keller TJ, Oppenheimer NJ. Enhanced bleomycin-mediated damage of DNA opposite charged nicks. A model for bleomycin-directed double strand scission of DNA. J Biol Chem. 1987 Nov 05; 262(31):15144-50.

Kam BL, Malver O, Marschner TM, Oppenheimer NJ. Pyridine coenzyme analogues. Synthesis and characterization of alpha- and beta-nicotinamide arabinoside adenine dinucleotides. Biochemistry. 1987 Jun 16; 26(12):3453-61.

Ehrenfeld GM, Shipley JB, Heimbrook DC, Sugiyama H, Long EC, van Boom JH, van der Marel GA, Oppenheimer NJ, Hecht SM. Copper-dependent cleavage of DNA by bleomycin. Biochemistry. 1987 Feb 10; 26(3):931-42.

Burgner JW, Oppenheimer NJ, Ray WJ. Remote nitrogen-15 isotope effects on addition of cyanide to NAD. Biochemistry. 1987 Jan 13; 26(1):91-6.

Moss J, Oppenheimer NJ, West RE, Stanley SJ. Amino acid specific ADP-ribosylation: substrate specificity of an ADP-ribosylarginine hydrolase from turkey erythrocytes. Biochemistry. 1986 Sep 23; 25(19):5408-14.

Oppenheimer NJ. The stereospecificity of oxidation of alpha-[4R-2H]NADH by dehydrogenases. J Biol Chem. 1986 Sep 15; 261(26):12209-12.

Kosen PA, Scheek RM, Naderi H, Basus VJ, Manogaran S, Schmidt PG, Oppenheimer NJ, Kuntz ID. Two-dimensional 1H NMR of three spin-labeled derivatives of bovine pancreatic trypsin inhibitor. Biochemistry. 1986 May 06; 25(9):2356-64.

Carroll SF, McCloskey JA, Crain PF, Oppenheimer NJ, Marschner TM, Collier RJ. Photoaffinity labeling of diphtheria toxin fragment A with NAD: structure of the photoproduct at position 148. Proc Natl Acad Sci U S A. 1985 Nov; 82(21):7237-41.

Ehrenfeld GM, Rodriguez LO, Hecht SM, Chang C, Basus VJ, Oppenheimer NJ. Copper(I)-bleomycin: structurally unique complex that mediates oxidative DNA strand scission. Biochemistry. 1985 Jan 01; 24(1):81-92.

Oppenheimer NJ. ADP-ribosylarginine. Methods Enzymol. 1984; 106:399-403.

Barr PJ, Oppenheimer NJ, Santi DV. Thymidylate synthetase-catalyzed conversions of E-5-(2-bromovinyl)-2'-deoxyuridylate. J Biol Chem. 1983 Nov 25; 258(22):13627-31.

Oppenheimer NJ, Bodley JW. Diphtheria toxin. Site and configuration of ADP-ribosylation of diphthamide in elongation factor 2. J Biol Chem. 1981 Aug 25; 256(16):8579-81.

Eberhard A, Burlingame AL, Eberhard C, Kenyon GL, Nealson KH, Oppenheimer NJ. Structural identification of autoinducer of Photobacterium fischeri luciferase. Biochemistry. 1981 Apr 28; 20(9):2444-9.

Cook PF, Oppenheimer NJ, Cleland WW. Secondary deuterium and nitrogen-15 isotope effects in enzyme-catalyzed reactions. Chemical mechanism of liver alcohol dehydrogenase. Biochemistry. 1981 Mar 31; 20(7):1817-25.

Oppenheimer NJ, Rodriguez LO, Hecht SM. Metal binding to modified bleomycins. Zinc and ferrous complexes with an acetylated bleomycin. Biochemistry. 1980 Aug 19; 19(17):4096-103.

Moss J, Stanley SJ, Oppenheimer NJ. Substrate specificity and partial purification of a stereospecific NAD- and guanidine-dependent ADP-ribosyltransferase from avian erythrocytes. J Biol Chem. 1979 Sep 25; 254(18):8891-4.

Oppenheimer NJ, Rodriguez LO, Hecht SM. Proton nuclear magnetic resonance study of the structure of bleomycin and the zinc-bleomycin complex. Biochemistry. 1979 Aug 07; 18(16):3439-45.

Moss J, Garrison S, Oppenheimer NJ, Richardson SH. NAD-dependent ADP-ribosylation of arginine and proteins by Escherichia coli heat-labile enterotoxin. J Biol Chem. 1979 Jul 25; 254(14):6270-2.

Arnold LJ, Oppenheimer NJ, Lee CY, Kaplan NO. Proton nuclear magnetic resonance study of the conformation and configuration of the cyclized pyridine nucleotide adducts. Biochemistry. 1979 Jun 26; 18(13):2787-93.

Oppenheimer NJ. The stereospecificity of pig brain NAD-glycohydrolase-catalyzed methanolysis of NAD. FEBS Lett. 1978 Oct 15; 94(2):368-70.

Oppenheimer NJ. Structural determination and stereospecificity of the choleragen-catalyzed reaction of NAD+ with guanidines. J Biol Chem. 1978 Jul 25; 253(14):4907-10.

Oppenheimer NJ, Arnold LJ, Kaplan NO. Stereospecificity of the intramolecular association of reduced pyridine coenzymes. Biochemistry. 1978 Jun 27; 17(13):2613-9.

Oppenheimer NJ, Kaplan NO. Proton magnetic resonance study of the intramolecular association and conformation of the alpha and beta pyridine mononucleotides and nucleosides. Biochemistry. 1976 Sep 07; 15(18):3981-9.

Kasai H, Oashi Z, Harada F, Nishimura S, Oppenheimer NJ, Crain PF, Liehr JG, von Minden DL, McCloskey JA. Structure of the modified nucleoside Q isolated from Escherichia coli transfer ribonucleic acid. 7-(4,5-cis-Dihydroxy-1-cyclopenten-3-ylaminomethyl)-7-deazaguanosine. Biochemistry. 1975 Sep 23; 14(19):4198-208.

Oppenheimer NJ, Kaplan NO. The alpha beta epimerization of reduced nicotinamide adenine dinucleotide. Arch Biochem Biophys. 1975 Feb; 166(2):526-35.

Oppenheimer NJ, Kaplan NO. Glyceraldehyde-3-phosphate dehydrogenase catalyzed hydration of the 5-6 double bond of reduced beta-nicotinamide adenine dinucleotide (betaNADH). Formation of beta-6-hydroxy-1,4,5,6-tetrahydronicotinamide adenine dinucleotide. Biochemistry. 1974 Nov 05; 13(23):4685-94.

Oppenheimer NJ, Kaplan NO. Structure of the primary acid rearrangement product of reduced nicotinamide adenine dinucleotide (NADH). Biochemistry. 1974 Nov 05; 13(23):4675-85.

Lee CY, Oppenheimer NJ, Kaplan NO. Proton relaxation studies of diphosphopyridine coenzymes. Biochem Biophys Res Commun. 1974 Sep 23; 60(2):838-44.

Oppenheimer NJ. The primary acid product of DPNH. Biochem Biophys Res Commun. 1973 Feb 05; 50(3):683-90.

Oppenheimer NJ, Arnold LJ, Kaplan NO. A structure of pyridine nucleotides in solution. Proc Natl Acad Sci U S A. 1971 Dec; 68(12):3200-5.