Analytical methods and Chromatography
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1 Analytical methods and Chromatography Tinaïg Le Costaouëc Chromatography Service : Claire Boisset-Helbert (Scientific Supervisor) Laurine Buon (Technical Supervisor) Philippe Colin-Morel (Technician) Eric Bayma (Engineer assistant)
2 Polysaccharide HO Polymer of carbohydrates, linear or branched Composition : Neutral residue Acidic residue Hexosamines Substituents : organic, inorganic 2 Alage4a-b - Workshop - Grenoble 2017
3 HO Homopolysaccharides : one type of monosaccharide cellulose, amylose, dextran... HO Heteropolysaccharides : at least two types of different monosaccharides galactomannan, arabinoxylan, alginate 3 Alage4a-b - Workshop - Grenoble 2017
4 Origin Seaweeds Alginate, fucoidans Plants Cellulose Animals Chitin O HO CH 2 O NHAc HO O NHAc O CH 2 O HO CH 2 O NHAc 4 Alage4a-b - Workshop - Grenoble 2017
5 Bacteria Microalgae Fungi 5 Alage4a-b - Workshop - Grenoble 2017
6 Polysaccharide Applications 6 Alage4a-b - Workshop - Grenoble 2017
7 1 - Analysis of native polysaccharide Polysaccharide Applications 7 Alage4a-b - Workshop - Grenoble 2017
8 OD (595 nm) DO OD (480 nm) DO Overall composition Colorimetric assays Dosage of total carbohydrates : Dubois method (1956) 2,500 2,000 Gamme étalon (dosage sucres) Standard curve with glucose 1,500 1,000 y = 0,0433x R 2 = 0,9896 0,500 0, Quantity Quantité (µg) (µg) Dosage of proteins : Bradford method (1976) Gamme etalon (dosage protéines) 0,800 0,700 0,600 0,500 0,400 0,300 0,200 0,100 Standard curve with Bovin Serum Abumin y = 0,0344x R 2 = 0,9826 0, Quantity Quantité (µg) 8 Alage4a-b - Workshop - Grenoble 2017
9 Composition Neutral carbohydrates Mass percentage Uronic acids proteins Sulfate groups Polysaccharide Carbohydrate content = 60% Carbohydrate content : from 1% to 85 % 9 Alage4a-b - Workshop - Grenoble 2017
10 Characterization of polysaccharides HO Molecular weight Chemical composition Structural elucidation Chromatography 10 Alage4a-b - Workshop - Grenoble 2017
11 Chromatography Eluent Pump Injector Detector Columns Control and data analysis 11 Alage4a-b - Workshop - Grenoble 2017
12 Molecular weight HPSEC with double detection: - Differential refractometer - MALLS Da Da - Polydispersity Index PDI = Mw / Mn Chromatogram of a mixture of pullulans eluted on SB-803pak and SB804pak shodex columns in series 0,2M sodium nitrate The PDI reflects the heterogeneity of molecular weight distribution of polysaccharide chains 12 Alage4a-b - Workshop - Grenoble 2017
13 Carbohydrate composition Nature of glycosidic residues GC, IC (HPAEC-PAD), NMR 4)- -D-Glcp-(1 4)-a-D-GalpA-(1 4)-a-D-Galp-(1 3 1 a-d-glcpa 3 1 -D-GlcpA 4 1 4,6-Pyr- -D-Manp 13 Alage4a-b - Workshop - Grenoble 2017
14 Carbohydrate composition - Neutral carbohydrates CH 2 O D-glucose D-galactose D-mannose CH 3 O L-fucose L-rhamnose - Uronic acids - Hexosamines CO O D-glucuronic acid D-galacturonic acid CH 2 O NHAc N-acetyl-D-glucosamine N-acetyl-D-galactosamine 14 Alage4a-b - Workshop - Grenoble 2017
15 Polysaccharide Total depolymerization Derivatization or not Analysis - GC - IC (HPAEC-PAD) 15 Alage4a-b - Workshop - Grenoble 2017
16 Carbohydrate composition Gas Chromatography : Principle Total hydrolysis + + derivatization Analysis by GC + + Gas chromatograph AGILENT with Flame Ionisation Detection (FID) - or coupled with mass spectrometry 16 Alage4a-b - Workshop - Grenoble 2017
17 Gas Chromatography : Derivatization Preparation of Trimethylsilylated derivatives (TMS) of polysaccharides Preparation of Alditol acetates of polysaccharides HO O O HO O O HO O HO O O HO O O HO O Methanolysis Me/HCl 3 N, 4 h, 100 C Hydrolysis TFA 2N or H 2 SO 4 2N, 4h, 100 C HO HO O O Me + HO HO O O Me HO HO + HO HO Trimethylsilylation Pyridin + Sylon BSTFA TMCS 99:1, 12 h, room Tp Reduction and acetylation NaBH 4 /pyridin, acetic anhydrid OTms O Tms O Tms OMe O + OTms Tms O Tms O OTms O OMe OTms OAc OAc AcO OAc AcO + OAc AcO AcO OAc OAc OAc OAc 17 Alage4a-b - Workshop - Grenoble 2017
18 Gas Chromatography : Principle or Flame Ionization detector 30 m X 0.53 mm, 0.2 µm id 18 Alage4a-b - Workshop - Grenoble 2017
19 Gas Chromatography : Alditol acetate derivatization AGILENT 6850 with Mass Spectrometry Detection Separation of alditol acetates of monosaccharides injected on a Supelco SP-2380 column, with helium as vector gas Identification and quantification of neutral sugars and hexosamines One peak for one type of sugar 19 Alage4a-b - Workshop - Grenoble 2017
20 Ara Man Rha Ara Ara Gal GalNAc GalNAc GlucNAc GalNAc Gal Glc Ara Gal GalNAc GlucNAc Man Glc Gas Chromatography : Trimethylsilylation derivatization AGILENT 6850 with Flame Ionisation Detection (FID) Separation of trimethylsilylated monosaccharides of hydrolysed polysaccharide injected on a HP5-MS column, with nitrogen as vector gas Myo-inositol????? Identification and quantification of neutral sugars, hexosamines and uronic acids Between one and four peaks for one type of sugar 20 Alage4a-b - Workshop - Grenoble 2017
21 High Perfomance Anion exchange Chromatography (HPAEC) CarboPac column Construction Core Sulfonated surface Ion-Exchange Surface Quaternary ammonium functionalized latex High ph: ionized carbohydrates Na NaOAc eluents 21 Alage4a-b - Workshop - Grenoble 2017
22 Galacturonique acid HPAEC-PAD Analysis of carbohydrate without derivatization Ionic chromatography DIONEX with Pulsed Amperometry Detection Separation of monosaccharides on a CarboPac PA1 column (Dionex) eluted with a Na/NaOAc gradient 95 nc ETALONNAGE-TFA #4 Etalon 4 ED_ rha arabi gala glucose 6 - ma xyl r fucose - 8, rhamnose - 16, arabinose - 18, galactose - 25, glucose - 28, xylose - 31, ribose - 38, , Acide Gal - 45, Acide glc - 46, , , , ,834-6 min 4,3 6,0 8,0 10,0 12,0 14,0 16,0 18,0 20,0 22,0 24,0 26,0 28,0 30,0 32,0 34,0 36,0 38,0 40,0 42,0 44,0 46,0 48,4 22 Alage4a-b - Workshop - Grenoble 2017
23 Linkages analysis O 2 1 Position of substituents GC/MS 4)- -D-Glcp-(1 4)-a-D-GalpA-(1 4)-a-D-Galp-(1 3 1 a-d-glcpa 3 1 -D-GlcpA 4 1 4,6-Pyr- -D-Manp Nature of glycosidic linkages GC/MS and NMR Linkage ose/ose 4? 3? Linkage ose/substituent 4? 3? Cyclic form of residues p or f GC/MS 23 Alage4a-b - Workshop - Grenoble 2017
24 Linkage analysis - methylation and GC/MS PMAA Partially methylated alditol acetates 24 Alage4a-b - Workshop - Grenoble 2017
25 GC / MS of PMAA derivatives GC Ribose linked in C2 : 1,2,4-tri-O-acetyl-1-deuterio-3,5-di-O-methyl-D-ribitol Myo-inositol MS HDCOAc 161 OAc OMe OAc 190 H2COMe 25 Alage4a-b - Workshop - Grenoble 2017
26 Corresponding substituted residue Type of monosaccharide Alditol acetates partially methylated Primary fragments (m/z) Corresponding substituted residu Fucose 1,5-di-O -acétyl-2,3,4-tri-o -méthyl-fucitol Fucp -(1-> Rhamnose 1,5-di-O -acétyl-2,3,4-tri-o -méthyl-rhamnitol Rhap -(1-> 1,2,5-tri-O -acétyl-3,4-di-o -méthyl-rhamnitol et/ou 1,4,5-tri-O -acétyl-2,3-di-o -méthyl-rhamnitol et/ou >2) et/ou 4)-Rhap -(1-> 1,3,5-tri-O -acétyl-2,4-di-o -méthyl-rhamnitol >3)-Rhap -(1-> 1,3,4,5-tri-O -acétyl-2-o -méthyl-rhamnitol >3,4)-Rhap -(1-> 1,2,3,5-tri-O -acétyl-4-o -méthyl-rhamnitol >2,3)-Rhap -(1-> Glucose 1,5-di-O -acétyl-2,3,4,6-tétra-o -méthyl-glucitol Glcp -(1-> a 1,4,5-tri-O -acétyl-2,3,6-tri-o -méthyl-glucitol >4)-Glcp -(1-> Galactose 1,5-di-O -acétyl-2,3,4,6-tétra-o -méthyl-galactitol Galp -(1-> 1,3,5-tri-O -acétyl-2,4,6-tri-o -méthyl-galactitol >3)-Galp -(1-> 1,4,5-tri-O -acétyl-2,3,6-tri-o -méthyl-galactitol >4)-Galp -(1-> b 1,3,5,6-tétra-O -acétyl-2,4-di-o -méthyl-galactitol >3,6)-Galp-(1-> Mannose 1,5-di-O -acétyl-2,3,4,6-tétra-o -méthyl-mannitol Manp -(1-> a 1,4,5-tri-O -acétyl-2,3,6-tri-o -méthyl-mannitol >4)-Manp -(1-> b 1,2,3,5-tétra-O -acétyl-4,6-di-o -méthyl-mannitol >2,3)-Manp -(1-> Glucuronic acid 1,5,6-tri-O -acétyl-2,3,4-tri-o -méthyl-6-d 2 -glucitol GlcpA -(1-> 1,3,5,6-tétra-O -acétyl-2,4-di-o -méthyl-6-d 2 -glucitol >3)-Glcp A-(1-> 1,4,5,6-tétra-O -acétyl-2,3-di-o -méthyl-6-d 2 -glucitol >4)-Glcp A-(1-> Galacturonic acid 1,3,4,5,6-tétra-O -acétyl-2-di-o -méthyl-6-d 2 -galactitol >3,4)-Galp A-(1-> Ramifications and/or Substituents 26 Alage4a-b - Workshop - Grenoble 2017
27 Substituents Nature and position of substituents EA, IC, IR and NMR 4)- -D-Glcp-(1 4)-a-D-GalpA-(1 4)-a-D-Galp-(1 3 1 a-d-glcpa 3 1 -D-GlcpA 4 1 4,6-Pyr- -D-Manp 27 Alage4a-b - Workshop - Grenoble 2017
28 Substituents Ionic chromatography Dionex with Conductimetric detection Separation of organic acids and inorganic groups on IonPac AS11 column (Dionex) eluent: Na gradient 28 Alage4a-b - Workshop - Grenoble 2017
29 Elemental analysis: Central Analysis Service of Lyon Inorganic substituents : Sulfate, phosphate content SO 3 - Lactate 1D/2D NMR Organic substituents : Lactate, pyruvate, succinate Lac Pyruvate Pyr ppm 1 H NMR spectra of native bacterial EPS (70 C, 500 MHz) 29 Alage4a-b - Workshop - Grenoble 2017
30 Laminarin FT-IR spectroscopy O-H C-H Sulfated Laminarin C=O C-O C-O-S S=O 30 Alage4a-b - Workshop - Grenoble 2017
31 Full structure / Sequence Analysis by Nuclear Magnetic Resonance (NMR) Anomeric configuration a / Presence and position of substituents 4)- -D-Glcp-(1 4)-a-D-GalpA-(1 4)-a-D-Galp-(1 3 1 a-d-glcpa 3 1 -D-GlcpA 4 1 4,6-Pyr- -D-Manp Linkages position 4 3 Sequence Alage4a-b - Workshop - Grenoble 2017
32 Analysis by Nuclear Magnetic Resonance (NMR) 1 H, 13 C COSY, TOCSY HSQC, HMBC 32 Alage4a-b - Workshop - Grenoble 2017
33 Analysis by Nuclear Magnetic Resonance (NMR) 1 H, 13 C COSY, TOCSY HSQC, HMBC H6a-6b/C6 Substituted Anomeric HSQC NMR spectrum of microalgae polysaccharide (55 C, 400 MHz) 33 Alage4a-b - Workshop - Grenoble 2017
34 2 - Analysis after depolymerisation Polysaccharide Applications 34 Alage4a-b - Workshop - Grenoble 2017
35 Partial depolymerization 1. Native polysaccharide analysis 2. Partial depolymerisation 3. Fractionation 4. Oligosaccharidic fraction analysis Structure 35 Alage4a-b - Workshop - Grenoble 2017
36 Depolymerization of polysaccharides Enzyme hydrolysis Specific degradations Chemical hydrolysis Non specific degradations Methanolysis (Me/HCl) Acidic hydrolysis (HCl, H 2 SO 4, TFA ) Radical Hydrolysis (H 2 O 2 ) Specific degradations Smith degradation -Elimination Lithium degradation 36 Alage4a-b - Workshop - Grenoble 2017
37 Purification of oligosaccharides Size Exclusion Chromatography (SEC) Largest molecules Excluded Separated smallest molecules Late elution Exclusion Gel granule Pores in the granule gel Elution with Vo 37 Alage4a-b - Workshop - Grenoble 2017
38 Size Exclusion Chromatography Separation and purification of maltodextrins from DP1 to DP10 on a Biogel P2, elution with H 2 O 38 Alage4a-b - Workshop - Grenoble 2017
39 HPAEC-PAD for Oligosaccharides separation Ionic chromatography DIONEX with Pulsed Amperometry Detection Separation of maltodextrins from DP 2 to DP 7 on a CarboPac PA1 column (Dionex) eluted with Na/NaOAc gradient maltod (1à7) #1 [modified by Administrateu maltod DP:1à7 ED_ nc maltose - 24, maltotriose - 27, maltotétraose - 30, maltopentaose - 32, maltohexaose - 34, maltoheptaose - 36, , , min 14,3 16,3 17,5 18,8 20,0 21,3 22,5 23,8 25,0 26,3 27,5 28,8 30,0 31,3 32,5 33,8 35,0 36,3 37,5 38,8 40,0 41,3 43,0 39 Alage4a-b - Workshop - Grenoble 2017
40 Oligosaccharide Analysis Carbohydrate composition (GC) Linkages analysis (GC/MS) Sequence D/2D NMR Mass spectrometry (ESI-IT, MALDI-TOF) 40 Alage4a-b - Workshop - Grenoble 2017
41 3 - Example: Structure of a microalgae Cell wall polysaccharide Polysaccharide Applications 41 Alage4a-b - Workshop - Grenoble 2017
42 Purification Microalgae powder Soxhlet extraction Ethanol, then acetone Residue 66 % w/w Oven 60 C overnight Residue 58 % w/w Water-80 C-2h X2 Residue Filtration 0.45µm lyophilisation Storage polysaccharide (β-glucan) 12 % w/w Chlorite (80 C, 3h) / Na 1% (RT,1h) Na 4% (100 C, 45 min) Residue X3 Cell wall polysaccharide 3-5 % w/w Concentration, dialysis 1kDa, filtration 0.45 µm, lyophilisation 42 Alage4a-b - Workshop - Grenoble 2017
43 Native cell wall polysaccharide analysis Colorimetric assays - Total sugar: Dubois - Proteins: Bradford assay - Sulfate groups: elemental analysis (EA) Molecular weight HPSEC/MALLS Total sugar % w/w Proteins % w/w Sulfate groups % w/w Mw g/mol Cell wall Polysacch aride 51,3 ± 4,7 7,0 ± 1,5 5, Alage4a-b - Workshop - Grenoble 2017
44 Native cell wall polysaccharide Carbohydrate composition: GC Trimethylsilyl derivatives preparation Man / GlcA 4,5 / 1 Linkage analysis: GC/MS Partially methylated alditol acetates preparation (Hakomori, 1964) Residue type % of total residues Manp-(1 2,0 3)-Manp-(1 60,5 2,3)-Manp-(1 31,7 44 Alage4a-b - Workshop - Grenoble 2017
45 Depolymerization Partial depolymerization Non specific degradations Acidic hydrolysis Specific degradations Smith degradation Fractionation Analysis 45 Alage4a-b - Workshop - Grenoble 2017
46 Microalgae cell wall polysaccharide structure Smith degradation / Fractionation NaIO 4 50 mm NaIO 4 oxidation, hydrolysis 1,5% Acetic acid, 2h, 100 C NaBH 4 H 3 O + H 3 O + Toyopearl HW-40 Gel 16/100, NH 4 OAc 0.1M, 0.4 ml/min 46 Alage4a-b - Workshop - Grenoble 2017
47 Microalgae cell wall polysaccharide structure Mild acid hydrolysis / Fractionation Hydrolysis 0.2 N TFA, 2h, 100 C 1 st purification: Superdex 30 HiLoad 26/600, Ammonium carbonate 0.1M, 1.5 ml/min 2 nd purification: 3 Superdex 30 HiLoad 26/600, Ammonium carbonate 0.1M, 1.5 ml/min 47 Alage4a-b - Workshop - Grenoble 2017
48 Microalgae cell wall polysaccharide structure Mild acid hydrolysis Smith degradation Analysis of the fractions GC GC/MS 2D NMR 48 Alage4a-b - Workshop - Grenoble 2017
49 NMR Fractions after mild acid hydrolysis 1 H- 13 C HMBC spectra 1 H spectra DP2 2 3 DP DP H NMR spectra of (A) DP2, (B) DP3 and (C) DP5 fractions recovered after mild acid hydrolysis and size-exclusion purification of the microalgae cell wall polysaccharide (D2O, 25 C, 400 MHz) Partial 1 H- 13 C HMBC spectra of (A) polysaccharide after Smith Degradation (D 2 O, 50 C, 500 MHz, with cryoprobe), (B) trisaccharide and (C) pentasaccharide, (D 2 O, 25 C, 400 MHz) 49 Alage4a-b - Workshop - Grenoble 2017
50 NMR Fractions after Smith degradation 1 H spectra Native polysaccharide SD Fraction 1 H NMR spectra of native and SD polysaccharide, D 2 O, 80 C, 500 MHz 50 Alage4a-b - Workshop - Grenoble 2017
51 Structure hypothesis Nature of glycosidic residues GC, NMR Nature of glycosidic linkages GC/MS and NMR 3)α-Man(1 3)α-Man(1 3)α-Man(1 3)α-Man(1 3)α-Man(1 3)α-Man(1 Anomeric configuration of glycosidic linkages NMR 2) β-glca 2) SO 3 Nature and position of substituents GC/MS, EA and NMR Sequence of glycosidic residues 2D NMR Many tools for polysaccharide structure analysis! 51 Alage4a-b - Workshop - Grenoble 2017
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