BlotGlyco O-GLYCAN SAMPLE PREPARATION KIT BS-45450Z

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1 BlotGlyco O-GLYCAN SAMPLE PREPARATION KIT BS-45450Z

2 CONTENTS Introduction... 3 Safety Information... 4 Notice... 4 Kit Components... 5 Required Equipment, Labware, and Reagents... 6 Reagents for BlotGlyco Operation... 6 Equipment and Labware for O-glycan release and BlotGlyco Operation... 6 Reagents for 2AB labeling (Optional)... 6 Schematic Workflow; refer to Operation for detailed procedures... 7 Operation: Step A. Releasing O-glycans from glycoproteins... 8 Operation (continued): Step B. Purification of released O-glycans... 9 Operation (continued): Step C. Labeling of reducing terminal of enriched O-glycans Application Data Ordering information BlotGlyco O-Glycan Sample Preparation Kit 2

3 Introduction This document provides information regarding the general use of the S-BIO BlotGlyco O-Glycan Sample Preparation Kit. The kit is designed for an efficient release and purification of O-linked glycans that attach to serine or threonine residue in glycoproteins. Recovered oligosaccharides possess a reducing end which is available for fluorescent labeling, such as 2-aminobenzamide (2AB) for HPLC assay or 8- aminopyrene-1,3,6-trisulfonate (APTS) for capillary electrophoresis (CE) analysis. Since the recovery of O- linked glycans from proteins is highly reproducible and proportional to the amount of materials subjected with the kit, it allows robust analyses of O-linked glycans existing in glycoconjugates in a variety of sample sources including purified glycoproteins. The kit operation includes two steps; 1) Mild chemical release of O-linked glycans to prevent sialic acid decomposition and to minimize the undesirable peeling products by a side reaction. 2) Purification of released oligosaccharides using a BlotGlyco bead where sugar molecules are chemoselectively enriched and recovered as free glycan or a labeled glycan with streamlined labeling procedure (optional Step C). BlotGlyco bead is a polymer-based particle that is densely functionalized with hydrazide groups in order to selectively capture oligosaccharides with reducing end at the termini. The covalent bond formed between the bead and an oligosaccharide enables thorough removal of contaminants, such as peptides/ proteins, lipids, salt, etc., making the kit one of the most effective glycan purification tools. Unlike other purification modules applying solid phase extraction, smaller sugar molecules, e.g. mono- or disaccharides, are also enriched successfully with BlotGlyco because of the nature of chemical capturing. Since the bonding between sugar molecules and the bead is reversible under a certain condition, the oligosaccharides are released as reducing sugars which can be used for labeling with a tag of customer s choice thus allowing sensitive detection of recovered glycans in a preferred analytical method. Please note that the kit does not contain fluorescent tag and chemical reagents to label the reducing end of recovered oligosaccharides. The kit allows for users to choose a tag for labeling the recovered glycans depending upon user s analysis method, i.e. HPLC, mass spectrometry, CE, etc. BlotGlyco O-Glycan Sample Preparation Kit 3

4 Safety Information - This product is for LABORATORY USE ONLY. - Safely dispose of waste liquids according to the applicable laws and regulations. - Perform all procedures using appropriate personal safety protection (safety glasses and powder-free nitrile gloves), and where appropriate, in a fume hood. - In case of contact with eyes, rinse immediately with water and seek medical attention. - In case of contact with skin, rinse immediately with water. - If swallowed, spit out immediately and rinse mouth with water and seek medical attention. - Never use the product after its expiration date. Keep under the recommended storage conditions. - All other materials not included in this product should be handled according to the relevant safety information. Notice Product specifications and this protocol are subject to change without prior notice for product improvement. Although this protocol has been carefully prepared, feel free to contact us if you have any questions or feedback. S-BIO is committed to developing sensitive, robust, and rapid methods for manual and automation workflow in glycan analysis. us at info.s-bio@s-bio.com to discuss customized workplan and products in development. Contacts for inquiries info.s-bio@s-bio.com (US), or s-bio@sumibe.co.jp (Japan) Tel: (US), or (Japan) URL: or BlotGlyco O-Glycan Sample Preparation Kit 4

5 Kit Components - BlotGlyco bead, dried (Qty 1 for 10 tests) - Reaction cup for BlotGlyco reaction (Qty 10) - Cleanup column (Qty 10) - Sample tube (2 ml, Qty 10) - (this booklet, Qty 1) - Quick Reference Guide (Qty 1) - O-Glycan releasing reagent in reaction tube; Store at 4 C upon arrival. Recommended use in ventilated area (Qty 10) BlotGlyco bead, dried Reaction cup O-Glycan releasing reagent in reaction tube Cleanup column BlotGlyco O-Glycan Sample Preparation Kit Sample tube (2-mL) 5

6 Required Equipment, Labware, and Reagents [Customer needs to arrange/prepare] Reagents for BlotGlyco Operation - Acetic acid (AcOH) reagent grade - Acetic anhydride reagent grade - Acetonitrile (ACN) reagent grade - Guanidine hydrochloride reagent grade - Hydrochloric acid (HCl) reagent grade - Methanol (MeOH) reagent grade - Triethylamine (TEA) reagent grade Equipment and Labware for O-glycan release and BlotGlyco Operation mL sample tubes - Pipette and tips for 1000, 200, 20, 10, 2 µl - Heating block for use at 55 to 90 C - Vortex mixer - Microcentrifuge - Centrifugal evaporator, e.g. SpeedVac Reagents for 2AB labeling (Optional) - Dimethylsulfoxide (DMSO) reagent grade - 2-aminobenzamide (2AB) reagent grade - Sodium cyanoborohydride reagent grade - Acetic acid reagent grade BlotGlyco O-Glycan Sample Preparation Kit 6

7 Schematic Workflow; refer to Operation for detailed procedures [Bullet No. corresponds to the Step No. in Quick Reference Guide] A) Releasing O-glycans from glycoproteins 1. Add glycoprotein sample solution to a reaction tube containing O-Glycan releasing reagent. 2. Incubate at 55 C for 5 hr with the cap closed tightly. Releases glycans from proteins 3. Remove remaining reagents using a centrifugal vacuum evaporator at 60 C overnight. B) Purification of released sugars - Dissolve in 20 µl Milli-Q water. 4. Aliquot beads in a reaction cup. 5. Capture glycans on bead by incubating at 80 C for 1 hr. Incubate to dryness with lid open 6. Wash bead on centrifuge. 7. Block excess of functional groups on the bead at room temperature for 30 min. Use Acetic anhydride in MeOH 8. Wash bead on centrifuge. 9. liberate glycans from bead at 70 C for 1.5 hr. Incubate to dryness with lid open - Proceed to Step C for labeling the reducing terminal or elute glycans (reducing end-free) with water. C) Optional: Labeling the reducing end of purified glycans 10. Add a labeling reagent (dye) to the reaction cup. - Incubate 60 C for 2 hr; a typical reaction conditions for reductive amination. Pick one suited for your detection system among 2AB, APTS, etc. 11. Recover labeled glycans from the reaction cup. 12. Dilute the recovery with ACN, and condition the Cleanup column. 13. Remove excess of dye and reagents with the Cleanup column. 14. Add 50 µl of water, and collect the purified, labeled glycans with centrifuge, and store appropriately until use. BlotGlyco O-Glycan Sample Preparation Kit 7

8 Operation: Step A. Releasing O- glycans from glycoproteins Below are general procedures for utilizing the BlotGlyco O-Glycan Sample Preparation Kit for releasing of O-linked glycans validated using bovine fetuin. Notes (Read thoroughly before proceed to the experiment) Store unused O-glycan releasing reagent in a reaction tube in refrigerator (2 C 8 C) Operate O-glycan releasing reagent with ventilation or under a chemical hood O-glycan releasing reaction should be performed between 53 C 57 C. The conditions in the following guideline may require optimization for each user s sample. Step A. Releasing O-glycans from glycoproteins O-Glycan releasing reagent is preloaded in a reaction tube for your convenience 1. Add 20 µl of glycoprotein sample solution (>1 mg/ml recommended) to the reaction tube containing O-Glycan releasing reagent [Pipette the sample solution on top of the reagents]. Tighten cap. Mix well using a Vortex mixer and then spin down on centrifuge. mix spin down Suspension: A portion of solid reagent remains in the tube, making sample solution saturated with the reagent. 2. Incubate at 55 C for 5 hr on a heat block. After the reaction, it is typical that the reagent still exists as solid. 3. Uncap the tube (or pinhole the cap), and remove remaining reagents using a centrifugal vacuum evaporator, e.g. SpeedVac, at 60 C overnight. Tips: To remove effectively the releasing reagent, evaporation with heating at 60 C is highly recommended. BlotGlyco O-Glycan Sample Preparation Kit 8

9 Operation (continued): Step B. Purification of released O- glycans Below are general procedures for utilizing the BlotGlyco O-Glycan Sample Preparation Kit for purification of O-linked glycans released in Step A. User may want to follow optional fluorescent labeling of reducing terminal of glycans as described in Step C. Notes (Read the Operation thoroughly before proceed to the experiment) When dispersing BlotGlyco bead, never sonicate the beads. Sonication may cause bead decomposition. When aliquoting beads, disperse the bead suspension by pipetting several times and quickly transfer. BlotGlyco bead suspension should be stored at 4 C until use. A heating block should be placed in a fume hood to prevent inhalation of solvent vapor. Solutions to be prepared BlotGlyco bead suspension: Add 500 µl of Milli-Q water to a tube containing dried BlotGlyco bead, Store at 4 C until use. 2% (v/v) Acetic acid in acetonitrile: Mix 200 µl of acetic acid and 9.8 ml of ACN. 2 M Guanidine solution: Dissolve 1.9 g of guanidine hydrochloride in 10 ml of Milli-Q water 1% (v/v) Triethylamine in MeOH: Mix 100 µl of TEA and 9.9 ml of MeOH. 10% (v/v) Acetic anhydride in MeOH: Mix 100 µl of acetic anhydride with 900 µl of MeOH in a 1.5 ml tube; Prepare fresh before use. Step B. Purification of released sugars using a BlotGlyco bead 4. Reconstitute the dried material (Step A-3) in 20 µl of Milli-Q water, mix well, and spin down the solution on centrifuge. 5. While dispensing the beads, aliquot 50 µl of bead suspension in a bottom of reaction cup placed in a 2-mL sample tube [keep the tube for later use at washing, Step B-11]. 6. Centrifuge for 20 sec at 2,000 x g to remove water. 7. Transfer the reaction cup into a fresh 1.5 ml tube. 8. Add 180 µl of 2% (v/v) AcOH in ACN to the reaction cup. 9. Transfer the whole 20 µl of reconstituted glycan solution (Step B-4) to the reaction cup. 10. Capture glycans on bead by incubating the tube at 80 C for 1 hr on a heat block with the lid open to evaporate until dry. BlotGlyco O-Glycan Sample Preparation Kit 9

10 [if the beads are still wet after the reaction, continue the heating for 15 min to completely evaporate the solvent] 11. Transfer the reaction cup to a 2-mL sample tube and set in a bench top centrifuge. 12. Wash the beads* with 2 M guanidine aq. Add 200 µl of 2 M guanidine solution and centrifuge for 10 sec. 13. Repeat the wash with 2 M guanidine aq. once. 14. Wash the beads with 200 µl of Milli-Q water twice. 15. Wash the beads with 1% TEA in MeOH twice. 16. Place the reaction cup in a 1.5-mL tube. 17. Add 100 µl of 10% acetic anhydride in MeOH solution to block excess of functional groups on the bead at room temperature for 30 min. After the reaction, set the heat block at 70 C for the next reaction; Step B-24 *Glossary Wash beads : Add the designated solution into the reaction cup, then centrifuge for 5-10 sec at 2000 x g to remove the solution. Confirm that the solution has been completely removed. Occasionally, discard the waste liquid in the 2-mL tube 18. Transfer the reaction cup to a 2-mL sample tube and set in a bench top centrifuge. 19. Spin down for 5 sec to remove the MeOH solution. 20. Wash bead with 200 µl of Milli-Q water twice; remove water completely at the 2nd wash with a longer centrifuge (20 sec). 21. Transfer the reaction cup into a 1.5-mL tube. 22. Add 20 µl of Milli-Q water on the top of the beads. 23. Add 180 µl of 2% (v/v) AcOH in ACN to the reaction cup. 24. Incubate the tube at 70 C for 1.5 hr to liberate glycans from the bead with the lid open [if the beads are still wet after the reaction, continue the heating for 15 min to completely evaporate the solvent]. 25. Proceed to Step C for labeling the reducing terminal or elute glycans (reducing end-free) as in Step C-39, in case user needs a reducing sugar. After the reaction, set the heat block at 60 C for the next reaction; Step C-27 BlotGlyco O-Glycan Sample Preparation Kit 10

11 Operation (continued): Step C. Labeling of reducing terminal of enriched O- glycans Below are general procedures for labeling oligosaccharides at reducing terminal via reductive amination. Users interested in labeling the glycans with a tag, such as fluorescent 2AB, should follow the procedure below. Notes (Read thoroughly before proceed to the experiment) Sodium cyanoborohydride is a highly toxic chemical. Use protective equipment and operate in a fume hood. Smaller O-linked glycans such as monosaccharide and disaccharide have relatively weaker retention on the Cleanup column used in the removal of excess of reagents. Please pay attention on the loss of those glycans, if they are the sugars of interest. Solutions to be prepared 2AB reaction mix [350 mm 2AB, 1 M sodium cyanoborohydride in 30% acetic acid/dmso]: Dissolve 47.7 mg of 2AB in one ml of 30% (v/v) acetic acid in DMSO solution. Dissolve 62.8 mg of sodium cyanoborohydride in the 2AB solution. Mix vigorously by vortex. If the solid does not fully dissolve, heat the solution at 60 C for several minutes, then mix well. Note that tag and reagents are not included in the kit except for Cleanup column. Step C. Labeling of reducing terminal of enriched O-glycans 26. Add 50 µl of 2AB reaction mix to the reaction cup, do NOT close the lid. 27. Incubate at 60 C for 2 hr on a heat block with the tube lid open. 28. Transfer the reaction cup into a fresh 1.5-mL sample tube. 29. Collect labeled glycans in the reaction mixture from the reaction cup by centrifuging for 20 sec at 2,000 x g. 30. Dilute the reaction mixture (50 µl) by transferring to a 15-mL conical tube containing 4.95 ml of ACN [Adjust the ACN content to 99% (v/v)]. 31. Mix the diluted solution. Tips: Due to the low retention of monoand disaccharides, make ACN content up to 99%. 32. Insert the Cleanup column in a 2-mL tube. 33. Condition the Cleanup column by washing with 200 μl of Milli-Q water once and then twice with 200 μl of ACN, successively, using a benchtop centrifuge [If the lid hits the centrifuge, it can be cut off]. BlotGlyco O-Glycan Sample Preparation Kit 11

12 34. Take out the Cleanup column and 2-mL tube from the centrifuge, and then load 0.8 ml of the diluted sample letting the solution go through the column by gravity flow for 2 min. 35. Discard the waste liquid in 2-mL tube, and centrifuge briefly with slow and short spin, enough to go through the solution, e.g. 1,500 x g for 10 sec. 36. Add 600 μl of the remaining sample and centrifuge briefly as above. Repeat the sample load using a centrifuge until all the sample solutions get applied to the Cleanup column. Discard the waste occasionally as needed. 37. Add 600 μl of ACN, spin down by a centrifuge, and discard the waste liquid. 38. Repeat the above ACN wash once, discard the waste liquid. 39. Spin down to remove the solvent completely. 40. Place the column into a fresh 1.5-mL tube. 41. Add 50 μl of Milli-Q water into the Cleanup column [elution volume: up to 500 µl]. 42. Recover the labeled glycans by centrifuging for 20 sec at 2,000 x g and store the recovered glycans frozen until use. Notes on HPLC analysis of 2AB-labeled sugars The 2AB-label allows fluorescent detection of recovered glycans. Excitation wavelength: 330 nm / Emission wavelength: 420 nm. The collected solution contains a trace amount of acetonitrile. If acetonitrile affects the HPLC analysis, please dry the solution and redissolve in the appropriate solvent. Despite the cleanup process, a small amount of unreacted dye, 2AB, may remain in the solution. Therefore, a peak corresponding to 2AB dye may be observed in the HPLC analysis. BlotGlyco O-Glycan Sample Preparation Kit 12

13 Application Data 20 µg of bovine fetuin (20 µl of 1 mg/ml) was analyzed with BlotGlyco O-Glycan Sample Preparation Kit according to the above listed procedures. A representative fluorescent chromatogram is shown below, and revealed consistent results with previously reported O-glycan profiles for the glycoprotein. 2AB Intensities 2AB 2AB 2AB * We concluded that the peak shown with asterisk is an isomer of the adjacent trisaccharide, elu8on 8me is ~21.5 min. It may occur in some samples and condi8ons with less than 10% of adjacent parent peak. N-acetylgalactosamine (GalNAc) N-acetylglucosamine (GlcNAc) galactose (Gal) fucose (Fuc) N-acetylneuraminic acid (NeuAc) 2AB 2-aminobenzamide Analytical conditions LC system: Nexera, Shimadzu Column: ACQUITY UPLC BEH Glycan, 1.7 µm (2.1 x 150 mm) Column temp.: 40 C Flow rate: 0.2 ml/min Injection volume: 1 µl Fluorescence detection: Ex 330 nm/em 420 nm using an RF-20Axs Mobile phase A: 40% acetonitrile aq. containing 0.1% formic acid Mobile phase B: 90% acetonitrile aq. containing 0.1% formic acid Time (min) %A %B BlotGlyco O-Glycan Sample Preparation Kit 13

14 Ordering information Order No. Description Amount BS-45450Z BlotGlyco O-Glycan Sample Preparation Kit 10 tests Kit contents: Shipped at 4 C; Store at 4 C. BlotGlyco bead, O-Glycan releasing reagent in reaction tube, Reaction cup, Cleanup column, Sample tube (2 ml), Control glycoprotein solution, manual, Quick Reference Guide Related products - visit Order No. Description Amount BS-45403Z BlotGlyco 10, Glycan Purification and Labeling Kit 10 tests Kit contents: BlotGlyco bead, aowr tag*, Reaction cup, Cleanup column, BS-45404Z BlotGlyco 50, Glycan Purification and Labeling Kit 50 tests Kit contents: BlotGlyco bead, aowr tag*, Reaction cup, Cleanup column, BS-45413Z BlotGlyco 96 plate B, Glycan Purification and Labeling Kit 1 test for 96-well assay Kit contents: BlotGlyco bead, Filter plate, Cleanup plate, BS-45414Z BlotGlyco 10B, Glycan Purification and Labeling Kit 10 tests Kit contents: BlotGlyco bead, Reaction cup, Cleanup column, BS-45415Z BlotGlyco 50B, Glycan Purification and Labeling Kit 50 tests Kit contents: *aowr tag is designed for MALDI-TOF MS analysis. BlotGlyco bead, Reaction cup, Cleanup column, Related analytical services - visit Order No. Description Type of analysis GMX-001 GlycanMap Xpress analysis N-Glycan profiling BlotGlyco bead-based N-glycan purification following to PNGase F-catalyzed glycan release in a fully automated sample processing system with high-throughput MALDI-TOF MS analysis to generate rapid, reproducible glycan profiling report for glycoproteins; > 0.5% of total N-glycans are reported in µm. GMO-001 GlycanMap analysis for O-glycans O-Glycan profiling Reproducible chemical release of O-glycans followed by BlotGlyco-based glycan purification in a fully automated sample processing system with high-throughput MALDI-TOF MS analysis to generate reproducible O-glycan profiling report; O-Glycan species are reported in relative amount (% of total). GMF-001 GlycanMap analysis Detailed Glycan analysis Analysis of applicable biological fluids with S-BIO s automated sample processing system with highthroughput MALDI-TOF MS(/MS) analysis to generate a detailed report for client s needs; available for study of biomarker discovery, detailed glycan characterization of N- and O-glycans, and/or statistical analysis of glycan distribution, etc. BlotGlyco O-Glycan Sample Preparation Kit 14

15 Memo BlotGlyco O-Glycan Sample Preparation Kit 15

16 2015 S-BIO S-BIO, Vaupell Holdings Inc., Group Company of Sumitomo Bakelite Co., Ltd. Printed in the U.S.A. July 2015 Rev A

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