University of North Florida
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Stuart Chalk, Ph.D.
Department of Chemistry
University of North Florida
Phone: 1-904-620-1938
Fax: 1-904-620-3535
Email: schalk@unf.edu
Website: @unf

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Serine

  • IUPAC Name: (2S)-2-amino-3-hydroxypropanoic acid
  • Molecular Formula: C3H7NO3
  • CAS Registry Number: 56-45-1
  • InChI: InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1
  • InChI Key: MTCFGRXMJLQNBG-REOHCLBHSA-N

@ ChemSpider@ NIST@ PubChem

Citations 6

"Role Of Electron-donating/withdrawing Character, PH And Stoichiometry On The Chemiluminescent Reaction Of Tris-(2,2'-bipyridyl)ruthenium(III) With Amino-acids"
Anal. Chem. 1992 Volume 64, Issue 2 Pages 166-170
Stephen N. Brune and Donald R. Bobbitt

Abstract: The post-column detection of amino-acids by their chemiluminescent reaction with electrogenerated tris-(2,2'-bipyridyl)ruthenium(II)I (I) is described. Separation is carried out on a column (25 cm x 4.6 mm) of Partisil 10 SCX connected to the detection cell via a mixing tee. The detection cell consists of a small glass coil to which I, generated at 0.89 V vs. Ag wire from tris-(2,2'-bipyridyl)ruthenium(II), is delivered. For application to gramicidin D digest, the mobile phase (1 mL min-1) was 1 mM Na2SO4 (pH 2.5) and this was adjusted post-column to pH 10 with 0.05 M boric acid. Response was rectilinear over two orders of magnitude for leucine. Detection limits for serine and leucine were 135 and 3 pmol, respectively. The presence of electron-withdrawing groups on the α-carbon of the amino-acid decreases chemiluminescence and electron-donating groups increase chemiluminescence. A post-column chemiluminescent technique for the detection of underivatized amino acids using electrogenerated tris(2,2'-bipyridyl)ruthenium(III) is described. The reaction chemical has been investigated, and it has been shown that the electron withdrawing/donating character of the R group attached to the α-carbon of the amine influences the chemiluminescent efficiency of the reaction. Stoichiometric studies conducted on four amines produced a mole ratio of 2:1, ruthenium:amine. At optimum reaction conditions the relative intensities of the primary amino acids tested varied by a factor of 55, with serine yielding the lowest chemiluminescence and leucine yielding the highest chemiluminescence. Detection limits for serine and leucine have been calculated to be 135 and 3 pmol, respectively, at a S/N ratio of 3. Linearity has been demonstrated over 2 orders of magnitude for Leu. The ability to implement this system for post-column chemiluminescence detection of amino acids following a protein digest has been demonstrated.
HPLC Chemiluminescence Post-column derivatization Electrochemical reagent generation Optimization pH Stoichiometry

"Simultaneous Mixture Analysis Using A Dynamic Microbial Sensor Combined With Chemometrics"
Anal. Chem. 1996 Volume 68, Issue 21 Pages 3845-3850
Michael Slama, Christiane Zaborosch, Dietrich Wienke, and Friedrich Spener

Abstract: A biosensor consisting of Alcaligenes eutrophus micro-organisms immobilized on to a Clark-type O2 sensor was used in a FIA system for the analysis of binary mixture of gluconate/acetate and L-serine/L-threonine. The determination was based on the increased respiratory activity of the microbial cells in the presence of the analytes. The biosensor was fabricated by immobilizing the microbial cells within a polyurethane hydrogel and sandwiching this material between an inner polyethylene membrane and an outer capillary pore membrane (0.6 µm pore diameter; 10 µm thick) attached to the O2 electrode. The FIA system was operated with an alternating flow (100 ml/h) of 50 mM Tris-hydrochloride buffer of pH 7.2 and the sample in the same buffer. The O2 electrode vs. Pt cathode and Ag/AgCl reference electrode was polarized at -800 mV. Transient signals for the analyte mixtures were obtained by allowing the sample streams to flow for 25 or 30 s. The experimental data was analyzed by partial least squares using the software package ICB-PLS. The system was calibrated using a standard containing up to 40 mg/l gluconate/10 mg/l acetate and 10 mg/l L-serine/15 mg/l L-threonine. The root mean square errors of prediction for gluconate, acetate, L-serine and L-threonine were 1.67, 0.51, 0.85 and 1.31 mg/l, respectively.
Sensor Chemometrics Partial least squares

"Amino-acid Analysis By High Performance Liquid Chromatography Of A Single Stained Protein Band From A Polyacrylamide Gel"
Anal. Biochem. 1987 Volume 160, Issue 2 Pages 362-367
Yoko Hashimoto, Sadako Yamagata* and Taro Hayakawa*

Abstract: A single stained band containing ~5 µg of protein was cut from a polyacrylamide gel and hydrolyzed in the presence of mercaptoacetic acid. The hydrolysate was analyzed by HPLC at 55°C on a column (15 cm x 4 mm) of sulfonated polystyrene cation-exchange resin (7 µm) with a pre-column (25 cm x 4 mm) of Dowex 50W-16 resin and step gradient elution with 0.2 M Na citrate (pH 3.15) - ethanol (93:7), 0.6 M Na citrate (pH 10.0) and 0.2 M NaOH at 0.3 mL min-1. Fluorimetric detection was at 450 nm (excitation at 348 nm) after post-column derivatization with phthalaldehyde and NaClO. Ammonia did not interfere. The recovery of methionine was inconsistent and recoveries of tryptophan, isoleucine, threonine and serine were low. Bovine serum albumin, ribonuclease B, ovalbumin, pepsin and chymotrypsinogen A were analyzed by this method with good agreement with theoretical values.
Cow Serum HPLC Fluorescence Interferences Post-column derivatization

"Flow Injection Analysis System For The Supervision Of Industrial Chromatographic Downstream Processing In Biotechnology"
Biosens. Bioelectron. 1998 Volume 13, Issue 12 Pages 1251-1255
P. Sosnitzaa, F. Irtela, R. Ulbera, M. Busseb, R. Faurieb, L. Fischerc and T. Schepera,*

Abstract: Sugar beet molasses is a natural resource for various products used in daily life, ranging from sucrose to amino acids for pharmaceutical industry. The separation of molasses into these high value components is performed on a large scale by ion exchange/exclusion chromatography A biosensor system was set up for the 'in time' anal. of serine and sucrose during molasses desugarization. D-Serine was analyzed with the multi-enzyme system D-serine dehydratase/lactic dehydrogenase and photometric detection of the NADH consumed. Sucrose was determined with invertase/mutarotase/glucose oxidase and the oxygen consumed was monitored amperometrically. An anal. could be performed within 2-5 min by directly injecting samples from the chromatography process into the flow injection analysis system. The determination range for the sucrose anal. was 0-2.5 gl-1 and for the anal. of D-serine 0-0.5 gl-1. The standard deviation for the measurement of D-serine was 1.7%.
Food Amperometry Sensor Spectrophotometry HPLC Process monitoring Immobilized enzyme

"Fluorimetric Determination Of Amino-acids And Proteins Utilizing A Copper(II)-catalysed Reaction"
Bull. Chem. Soc. Jpn. 1991 Volume 64, Issue 12 Pages 3634-3638
Hisakazu Mori,Kazue Sakai,Kyoko Yamashina,Sayuri Hirata and Kumiko Horie

Abstract: Amino-acids were found to accelerate the Cu(II)-catalyzed oxidation of di-2-pyridyl ketone hydrazone (I) to form a fluorescent compound in acidic medium. With use of this enhancement effect, L-histidine, L-cysteine, L-glutamic acid, glycine, DL-serine and L-arginine were determined by flow injection analysis (diagram given). Sample was injected into a carrier stream of water which was merged with stream of 0.5 µM I - 0.1 M NaOH, passed through a reaction coil operated at 25°C, and mixed with a stream of 0.4 M HCl before fluorimetric detection at 435 nm (excitation at 349 nm). The detection limit of L-histidine was 2 pmol. The method was also used to determine proteins which were found to decrease the catalysis; the detection limit for bovine serum albumin was 20 ng.
Fluorescence Catalysis

"Electrochemiluminescence Detection Of Amino Acids And Peptides By Flow Injection Analysis"
Fenxi Kexue Xuebao 1998 Volume 14, Issue 4 Pages 278-282
Chen Xi, Masanori Sato

Abstract: A new electrochemiluminescence flow injection analysis system was studied for anal. for some amino acids, peptides and nitrogen compounds by using tris(2,2'-bipyridine)ruthenium(II) [Ru(bpy)32+]. The luminescence of Ru(bpy)32+, which was oxidized to Ru(bpy)33+ on the surface of glassy carbon electrode at +1.35 V (vs. Ag/AgCl) would be intensified with the injection of amino acid peptide or nitrogen compound The detection limits of the amino aids by this method ranged from 0.1 pmol of hydroxyproline and proline to 0.4 nmol of serine. Voltammetric anal. revealed the oxidation of Ru(bpy)32+ to Ru(bpy)33+ was nearly reversible and the light emission was caused by the excited state of Ru(bpy)32+. A reaction mechanism is proposed.
Chemiluminescence Electrode Indirect