Potential of Daughter Ion Mass Spectrometry (ESI-MS-CID) in the Analysis of Cationic and Methyl Starches
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1 Potential of Daughter Ion Mass Spectrometry (ESI-MS-CID) in the Analysis of Cationic and Methyl Starches Petra Mischnick, Wiebke Tüting, Roland Adden TU Braunschweig
2 Starch amorphous domain amorphous growth ring H H H H H H Amylose H H H crystalline growth ring crystalline lamellae Amylopectin H H H H H H H H H H H H H H H H H P.J. Jenkins, A.M. Donald, Int. J. Biol. Macromol., 17 (1995) 15-21
3 Cationic Starch Starch H N (CH ) Cl 2,-Epoxypropyl-trimethylammonium chloride ( QUAB ) [H ] H N (CH ) Cl Stärke 2-Hydroxy--trimethylammoniumpropylstarch Paste Dry Slurry Extruder BMVLE-Projekt, FNR, Cooperation with FhG IAP Golm and Südzucker/Agrana, Tulln
4 Monomer Composition of Cationic Starches Starch H N (CH ) Cl [H ] Starch H N (CH ) Cl % PA-8 SL-6 DR- DR-6 DR-1 EX-4 EX-7 EX-11 Samples: S. Radosta, W. Vorwerg, IAP-FhG Golm
5 Enzymatic Degradation of Starch Derivatives Cationic Starch in water Incubation with α-amylase (ph 6 / 52 C) Incubation with Glucoamylase (ph 4,66 / 52 C) Enzyme Inactivation Filtration Enzymatic Determination of Glucose Mass Spectrometry
6 ESI-MS of Cationic Starches Prepared under Various Conditions after Enzymic Degradation DS.-.12 Paste Slurry Extruder I Dry Extruder II Rel. Intens. [%] KL DS=,4 KL DS=,8 KL DS=,12 SL DS=, SL DS=,6 SL DS=,1 EX DS=, EX DS=,6 EX DS=,1 TR DS=, TR DS=,6 TR DS=,1 EX2 DS=, EX2 DS=,6 2/1 /1 /2 4/1 4/2 5/2 6/2 DP/n (number of substituents) EX2 DS=,1
7 ESI-MS after Enzymatic Degradation Intens. x1 6 /1 62,4 ESI-MS Cat. Starch DS.1 after enz. Hydrolysis 2 Assignment: DP/n Subst. 1 68,2 2/1 458, /2 4/2 449, 5/2 6/2 5, 4/1 611,4 782, m/z MS 2 Y 2 Z 2 Z 1 Y Z 2,4 A R R R R R R R Intens. x1 5, 2,5 R B 2 Y 2 44, 458,2 5,,2 A 56,4 M 62,4 R R R 2, 2,5A 1 B 1 C 1 2,4A 2 B 2 C 2,2A B C ESI-MS 2 of /1 W. Tüting 1,5 B 1 1, 278,1,5 296,1 2,4 A 2,2 A 2 B, A 98, 8,1 62, 5,, m/z
8 5 ESI-MS 2 Cationic Starches enzymatically degraded DP Comparison of Production Methods R R R R Y 2 Z 2 Z 1 Y Z R R 2,5A 1 B 1 C 1 2,4A 2 B 2 C 2,2A B C R R R R R Rel. Intens. [%] DS.-.12 Paste Slurry Extruder I Dry Extruder II 1 5,2 A 2,4 B,2 A, 2,4 A A Y 2 B 2 2 A 2 B 1 Fragment m/z
9 ESI-MS 2 Cationic Starches enzymatically degraded 5 25 Comparison of Production Methods DS.6 Position 2 6 Paste Slurry Extruder Dry Intens. [%] B,2,2 A 2,4 A, 2,4 A A Y 2 B 2 2 A 2 B 1
10 Fragmentation Pathways Glycoside Cleavage Y 2 -Fragment H H H R H H H H H H H H H H H H H H H H H R H H H R H H H H H H H H H H H H B 2 -Fragment H H H R H R
11 ESI-MS 2 ESI-MS n Cationic Starches enzymatically degraded DS.-.12 B 2 /Y 2 -Amylopectin* 1 Slurry 6 -Amylose* 4 Paste 2.5 Extruder Dry 1 Glucoamylase α-amylase wet Main products dry H B 2 Y 2 n n n n cationic Amylopectin Cationic Amylose terminal substituted Side chains Cationic Amylose *S. Radosta, W. Vorwerg FhG IAP Golm
12 ESI-MS 2 Cationic Starches enzymatically degraded 5 25 DS.6 Comparison of Production Methods Position 2 6 Paste Slurry Extruder Dry Intens. [%] B 1 5 B,2,2 A 2,4 A, 2,4 A A Y 2 B 2 2 A 2 B 1
13 ESI-MS 2 Cationic Starches enzymatically degraded 5 25 DS.6 Comparison of Production Methods Position 2 6 Paste Slurry Extruder Dry Intens. [%] B 1 5 B,2,2 A 2,4 A, 2,4 A A Y 2 B 2 2 A 2 B 1
14 Substituent Distribution over the Starch Granule crystalline growth ring Amylopectin crystalline lamellae amorphous domain amorphous growth ring H H H H H H Amylose H H H Extruder Dry strong DS-dependence
15 Substituent Distribution over the Starch Granule crystalline growth ring crystalline lamellae amorphous domain amorphous growth ring Amylopectin H H H H H H H H H H H H H H H H H Paste Slurry W. Tueting, K. Wegemann, P. Mischnick, Carbohydr. Res., 9 (24)
16 H H H Polymer Analogous Reaction k 2 k k 6 H H H H H H H H H DS = number of substituted H Glucose
17 Fragmentation of 2,,6-tri--methylated Trisaccharides with Me-d -Labelling 8 Rel. Intens. [%] ,2 A,2 A 2 m/z 2,,6-Me ,,6-Me-d 6 9 2,6-Me--Me-d ,-Me-6-Me-d ,6-Me-2-Me-d B,2 A 2,4 A Y 2 B 2,2 A 2 B 1 Fragment Reproducible Daughter Ion Mass Spectra Fragment Shifts according to the Deuteromethylated Positions
18 Monomer Analysis of Methyl Glucans by ESI-MS n ESI-MS 1 von MC Sample Preparation: - Perdeuteromethylation - Partial Hydrolysis DP m/z DP 1 a) DP DP m/z R. Adden
19 ESI-MS 1 Na -Adducts Monomer Analysis of Methyl Glucans by ESI-MS n % unsubstituted 1% trisubstituted m/z n(ch ) n(cd )
20 ESI-MS 1 Na -Adducts Monomer Analysis of Methyl Glucans by ESI-MS n ESI-MS : 1 ESI-MS 2 1 : m/z n(ch ) n(cd )
21 ESI-MS 2 of DP2 Evaluated fragments Intens Y1- MeH Y1 254 Na -adducts,2a H R R R R 6 R R 2 H H R R H m/z H R R R R R H B 1,2 A 2 -MeH(R H),2 A 2 Example: m/z Fragment m/z CH in 2 6,2 A R H analogous
22 ESI-MS 2 of DP2 Evaluated fragments Intens Y1- MeH Y1 254 Na -adducts,2a H R R R R 6 R R 2 H H R R H m/z H R R R R R H B 1,2 A 2 -MeH(R H),2 A 2 Example: m/z Fragment m/z CH in 2 6,2 A R H analogous
23 ESI-MS 2 von DP2 Evaluated fragments R R H R R 6 R R 2 H H R Intens R H 216 Y1-219 MeH 251 H Y1 254 R Na -Adducts R R,2A m/z R R H 464 B 1,2 A 2 -MeH(R H),2 A 2 Example: m/z Fragment m/z CH in 2 6,2 A R H analogous
24 ESI-MS 1 Li -adducts 9 49 m/z ESI-MS 2 Quantitative Monomer Analysis of Methyl glucans by ESI-MS n -Fragments ESI-MS n(ch ) n(cd ) m/z 2 1
25 ESI-MS of (Li-adducts) Quantitative Monomer Analysis of Methyl glucans by ESI-MS n H R 6 R R 2 Li H H R6 Li R H H R R 6 H Li R 6 Li Li H R R 2 (M) M-R 2 H,2 A 1, A 1, A m/z Rel. Intensity [%] 2,,6-Me 2,,6-Me-d 25 2,-Me-6-Me-d 2,6-Me--Me-d M-H 2 M-MeH,2 A 1, A, A 1, A -MeH,4 A 1
26 ESI-MS of (Li-adducts) Quantitative Monomer Analysis of Methyl glucans by ESI-MS n H R 6 R R 2 Li H H R6 Li R H H R R 6 H Li R 6 Li Li H R R 2 (M) M-R 2 H,2 A 1, A 1, A m/z Rel. Intensity [%] 2,,6-Me 2,,6-Me-d 25 2,-Me-6-Me-d 2,6-Me--Me-d M-H 2 M-MeH,2 A 1, A, A 1, A -MeH,4 A 1
27 ESI-MS of (Li-adducts) Quantitative Monomer Analysis of Methyl glucans by ESI-MS n H R 6 R R 2 Li H H R6 Li R H H R R 6 H Li R 6 Li Li H R R 2 (M) M-R 2 H,2 A 1, A 1, A m/z Rel. Intensity [%] 2,,6-Me 2,,6-Me-d 25 2,-Me-6-Me-d 2,6-Me--Me-d M-H 2 M-MeH,2 A 1, A, A 1, A -MeH,4 A 1
28 ESI-MS of (Li-adducts) Quantitative Monomer Analysis of Methyl-glucans by ESI-MS n H R 6 R R 2 Li H H R6 Li R H H R R 6 H Li R 6 Li Li H R R 2 (M) M-R 2 H,2 A 1, A 1, A m/z Rel. Intensity [%] 2,,6-Me 2,,6-Me-d 25 2,-Me-6-Me-d 2,6-Me--Me-d M-H 2 M-MeH,2 A 1, A, A 1, A -MeH,4 A 1
29 Monomer Analysis of Methylcelluloses by ESI-MS n Comparison of EDI-MS/CID and GC: Methylcellulose, DS ESI-MS n Hydrolysis/Reduction/Acetylation/GC Mol % Me in Position Roland Adden
30 Thank you for your kind attention
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32 Auswahl der Amplitude Intens. abs. Intens. abs. Kationische Stärke (DP ) 25 Ampl Maltotriose M,2 2,4 B,2 A 2,4 A Y 2 B 2 A 2 A 2 B 1 Fragment Ampl..45 Ampl..5 Ampl..55 Ampl..6 Ampl..65 Ampl..7 Ampl Ampl..6 M B,2,2 A 2,4 A Y 2 B 2 A 2 B 1 Fragment W. Tüting, K. Wegemann, P. Mischnick, Carbohydr. Res., 9 (24) Ampl..65 Ampl..7 Ampl..75 Ampl..8 Ampl..85 Ampl..9 Ampl..95
33 Analysis of Cationic Starch after Hofmann-Elimination H CH CH H H H N(CH ) CH CH CH GC-MS H H N Cl- CH CH CH CH CH Methanolysis Hofmann- Elimination -N(CH ) CH CH C H H H Permethylation CH CH H H Cl - N(CH ) CH CH CH N(CH) I - CH H H CH CH H H CH CH Cl- N CH CH CH CH CH I - N CH CH CH.Wilke, P. Mischnick
34 GC of Cationic Starch after Methanolysis, Permethylation and Hofmann-Elimination 2 2 CH CH CH CH FID Response CH x time [min]. Wilke, P. Mischnick
35 Analysis of Cationic Starch after N-Demethylation H H H H N(CH ) H Methanolysis H H Demethylation (Morpholine) H N Cl- CH CH CH Trimethylsilylation N(CH N(CH ) 2 ) 2 TMS H H TMS H CH CH TMS TMS H TMS H TMS H TMS CH H H - Cl N(CH ) CH H H H H CH Cl- N CH CH H CH CH GC-MS (m/z 58) TMS CH N CH H CH N CH V. Goclik, P. Mischnick, Carbohydr. Res. 8 (2) 7-741
36 GC of Cationic Starch after Methanolysis, N-Demethylation and Trimethylsilylation un- TMS TMS TMS CH DS.82 FID Response mono- TMS CH * N CH di- tri- tetra- time [min]
37 Enzymatic Degradation of Cationic Starches Intens. x1 6 /1 62,4 ESI-MS DP 1 DP 2 DP DP 4 DP 5 DP 6 DP 7 DP 8 DP 9 DP 1 DP 11 DP 12 1,25 1,,75,5 / 2/2 /2 7/4 4/2 6/ 2/1 458,2 5/2 7/ 1/4 449,,25 4/ 5/ 8/4 12/4 68,2 1/ 5,2 78,2 1/1 6/4 9/4 11/4 7/2 8/2 284,2 44,6 446, 611,4 5, 287,2 8,1 444,8 485, 8,2 92, 525,8 554,4 68,4 296,2 64, 566,5 662,5 692, 782,4 65,8 77,, m/z 8/ 6/2 9/ 4/1 Cationic Starch (DS N.24) after enzymatic degradation
38 Fragmentation of regioselectivly substituted ligosaccharides α-glucans, DP, R = CH Rel. Intens. [%] ,2 2,4,2 B A A Y 2 B 2 Y 2 - MeH Maltotriose 6-Me A 2 B 1 Rel. Intens. [%] Me,6-Me,2 2,4,2 B A A Y 2 B 2 Y 2 - A 2 B 1 MeH Rel. Intens. [%] Me 2,6-Me,2 2,4 B A A Y 2 B 2 Y 2 - MeH,2 A 2 B 1 7 2,-Me 6 R R 5 R 2,,6-Me 4 R R R R 2 1R R R 2,5 A,2 2,4 B,2 1 B C A 2,4 A A Y 2 B CY 2 - A,2 2 A B C Rel. Intens. [%] Y 2 Z 2 Z 1 Y Z R W. Tüting, R. Adden, P. Mischnick, Int. J. Mass Spectrom., 22 (24)
39 Fragmentation of regioselectivly substituted ligosaccharides α-glucans, DP2, R = CH Rel. Intens. [%] Maltose 6-Me Rel. Intens. [%] Me,6-Me B 2,2 A 2 2,4 A 2 B 1 - B 2,2 A 2 2,4 A 2 B 1 - MeH MeH Fragment Fragment Rel. Intens. [%] Me 2,6-Me Rel. Intens. [%] ,-Me 2,,6-Me B 2,2 A 2 2,4 A 2 B 1 - B 2,2 A 2 2,4 A 2 B 1 - MeH MeH W. Tüting, R. Adden, P. Mischnick, Int. J. Mass Spectrom., 22 (24)
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