Glycan Standards. For microarrays and the identification/ quantification of glycans. Cambridge Isotope Laboratories, Inc. isotope.

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1 Cambridge Isotope Laboratories, Inc. isotope.com RESEARCH PRDUCTS Glycan Standards For microarrays and the identification/ quantification of glycans The emerging field of glycomics focuses on the structure and function of glycans in biological systems. Glycans are chained carbohydrates that are free or conjugated to macromolecules, such as proteins (referred to as glycoproteins or lipids (referred to as glycolipids. They participate in a diverse array of biological processes (e.g., cell signaling, protein folding, and immune recognition and are implicated in a number of diseases (e.g., oncological, autoimmune, and Alzheimer s. While analytical methodologies for their detection and sequencing have advanced, glycomic research has been hampered by the lack of commercially available standards and research tools. Cambridge Isotope Laboratories, Inc. (CIL is pleased to offer high-quality standards to the glycomic research community to aid the detection, identification, and quantification of glycans. Specifically, these can be used as internal standards for mass spectrometry and as starting materials for glycomicroarrays. The glycan standards available are in 1 C -labeled and unlabeled forms. These encompass a broad range of categories (e.g., -linked, -linked, and fucosylated and have been highly characterized using a number of analytical techniques (e.g., 1 H MR, ESI-MS, and LC-MS. The standards are supplied as purified powders in 500 pmol quantities (bulk quantities available upon request. Please visit for more information. CIL, in partnership with Cassia, LLC, is pleased to offer custom synthesis of glycans. Please visit isotope.com to request a custom synthesis quote. Galactose ( 1 C ; Gal Galactose (Gal -Acetylgalactosamine (GalAc Glucose (Glc -Acetylglucosamine (GlcAc Mannose (Man -Acetylneuraminic acid (eu5ac Fucose (Fuc Figure. Symbol nomenclature for glycan standards and unlabeled monosaccharides, as recommended by the glycomics consortium network. 1 Reference 1. Varki, A; Cummings, R.D. et al Essentials of Glycobiology, nd edition. ISB-1: Glycans are synthesized and tested by Cassia, LLC.

2 Labeled CLM-1014-CA GLYCA-FX CLM CA GLYCA-F CLM CA GLYCA-F CLM CA GLYCA-F CLM CA GLYCA-F CLM-100-CA GLYCA-F CLM-1009-CA GLYCA-F CLM CA GLYCA-F CLM CA GLYCA-F CLM CA GLYCA--1C-GAL CLM CA GLYCA-FX-1C-GAL CLM-1009-CA GLYCA-F CLM CA GLYCA-F 88. Please visit isotope.com for pricing, ordering, and availability of other glycans. * Galactose ( 1 C Galactose -Acetylgalactosamine Glucose -Acetylglucosamine Mannose -Acetylneuraminic acid Fucose

3 CLM-1019-CA GLYCA--1C-GAL CLM CA GLYCA-F5-1C-GAL CLM-1018-CA GLYCA-15-1C-GAL CLM CA GLYCA-FX CLM-1011-CA GLYCA--1C-GAL4 CLM-1004-CA GLYCA-F-1C-GAL4 CLM CA GLYCA-F-1C-GAL4 CLM-101-CA GLYCA-1-1C-GAL CLM-1017-CA GLYCA-1-1C-GAL4 CLM CA GLYCA-FX5 CLM-1010-CA GLYCA-5-1C-GAL CLM CA GLYCA-5-1C-GAL CLM CA GLYCA-5-1C-GAL CLM-1010-CA GLYCA-F-1C-GAL CLM-1014-CA GLYCA-17-1C-GAL CLM-1015-CA GLYCA-17-1C-GAL4 CLM CA GLYCA-FX * Galactose ( 1 C Galactose -Acetylgalactosamine Glucose -Acetylglucosamine Mannose -Acetylneuraminic acid Fucose

4 Labeled CLM-1010-CA GLYCA-0-1C-GAL CLM-1011-CA GLYCA-0-1C-GAL CLM CA GLYCA--1C-GAL4 CLM-1011-CA GLYCA--1C-GAL CLM CA GLYCA-F CLM-101-CA GLYCA--1C-GAL, ([galactose- 1 C, 99%] β β CLM-101-CA GLYCA-19-1C-GAL CLM-101-CA GLYCA-19-1C-GAL CLM CA GLYCA-7-1C-GAL CLM CA GLYCA-7-1C-GAL CLM-1014-CA GLYCA-5-1C-GAL, ([galactose- 1 C, 99%] β β CLM CA GLYCA-F CLM-1011-CA GLYCA-1-1C-GAL CLM-1011-CA GLYCA-1-1C-GAL CLM-1015-CA GLYCA-4-1C-GAL,, ([galactose- 1 C, 99%] β β CLM-101-CA GLYCA--1C-GAL, ([galactose- 1 C, 99%] β β * Galactose ( 1 C Galactose -Acetylgalactosamine Glucose -Acetylglucosamine Mannose -Acetylneuraminic acid Fucose

5 CLM-1017-CA GLYCA-8-1C-GAL,, ([galactose- 1 C, 99%] β β CLM-1014-CA GLYCA-57-1C-GAL, ([galactose- 1 C, 99%] β β CLM CA GLYCA--1C-GAL CLM CA GLYCA--1C-GAL CLM-101-CA GLYCA-4-1C-GAL8,8 ([galactose- 1 C, 99%] β β CLM CA GLYCA-58-1C-GAL, ([galactose- 1 C, 99%] β β CLM-1015-CA GLYCA-5-1C-GAL,, ([galactose- 1 C, 99%] β β CLM-101-CA GLYCA-9-1C-GAL,, ([galactose- 1 C, 99%] β β CLM-1011-CA GLYCA-5-1C-GAL8,8 ([galactose- 1 C, 99%] β β CLM CA GLYCA-7-1C-GAL8,8 ([galactose- 1 C, 99%] β β CLM CA GLYCA-11-1C-GAL8,8 ([galactose- 1 C, 99%] β β CLM CA GLYCA-59-1C-GAL, ([galactose- 1 C, 99%] β β * Galactose ( 1 C Galactose -Acetylgalactosamine Glucose -Acetylglucosamine Mannose -Acetylneuraminic acid Fucose

6 Labeled CLM-1010-CA GLYCA--1C-GAL8,8 ([galactose- 1 C, 99%] CLM-1019-CA GLYCA--1C-GAL, ([galactose- 1 C, 99%] β β β β CLM CA GLYCA--1C-GAL,, ([galactose- 1 C, 99%] β β CLM-1015-CA GLYCA-70-1C-GAL,, ([galactose- 1 C, 99%] β 18. β CLM CA GLYCA-9-1C-GAL8,8 ([galactose- 1 C, 99%] β β CLM CA GLYCA-45-1C-GAL,, ([galactose- 1 C, 99%] β β CLM-1015-CA GLYCA-15-1C-GAL8,8 ([galactose- 1 C, 99%] β β CLM CA GLYCA-7-1C-GAL,, ([galactose- 1 C, 99%] β β CLM CA GLYCA-9-1C-GAL,, ([galactose- 1 C, 99%] β β * Galactose ( 1 C Galactose -Acetylgalactosamine Glucose -Acetylglucosamine Mannose -Acetylneuraminic acid Fucose

7 CLM-1014-CA GLYCA-71-1C-GAL,, ([galactose- 1 C, 99%] β β CLM-101-CA GLYCA-7-1C-GAL,, ([galactose- 1 C, 99%] β β CLM CA GLYCA-4-1C-GAL,, ([galactose- 1 C, 99%] β 41.5 β CLM CA GLYCA-1-1C-GAL8,8 ([galactose- 1 C, 99%] β β CLM-1014-CA GLYCA-48-1C-GAL,, ([galactose- 1 C, 99%] β β CLM CA GLYCA-5-1C-GAL,, ([galactose- 1 C, 99%] β β * Galactose ( 1 C Galactose -Acetylgalactosamine Glucose -Acetylglucosamine Mannose -Acetylneuraminic acid Fucose

8 Unlabeled ULM CA GLYCA-F78 (unlabeled 8.5 ULM-1007-CA GLYCA-F4 (unlabeled ULM CA GLYCA-F1 (unlabeled ULM-1009-CA GLYCA-F41 (unlabeled ULM-1005-CA GLYCA-F8 (unlabeled ULM-1010-CA GLYCA-F8 (unlabeled ULM-1007-CA GLYCA-F (unlabeled ULM CA GLYCA-F7 (unlabeled ULM-1018-CA GLYCA-1 (unlabeled ULM CA GLYCA-GLACAC (unlabeled ULM CA GLYCA-F4 (unlabeled 09.5 ULM CA GLYCA-F (unlabeled 09.5 ULM CA GLYCA-F5 (unlabeled 09.5 ULM-1008-CA GLYCA-F8 (unlabeled 4.59 * Galactose ( 1 C Galactose -Acetylgalactosamine Glucose -Acetylglucosamine Mannose -Acetylneuraminic acid Fucose

9 ULM CA GLYCA-F9 (unlabeled.58 ULM-1010-CA GLYCA-F0 (unlabeled 74.0 ULM CA GLYCA-F1 (unlabeled 74.0 ULM CA GLYCA-F81 (unlabeled ULM CA GLYCA-F44 (unlabeled ULM CA GLYCA-F8 (unlabeled ULM-1015-CA GLYCA-FX (unlabeled ULM CA GLYCA-F57 (unlabeled ULM CA GLYCA-F58 (unlabeled ULM CA GLYCA-F45 (unlabeled ULM-1005-CA GLYCA-F80 (unlabeled ULM-1008-CA GLYCA-F48 (unlabeled ULM CA GLYCA-F5 (unlabeled 8.7 ULM-1007-CA GLYCA-F0 (unlabeled * Galactose ( 1 C Galactose -Acetylgalactosamine Glucose -Acetylglucosamine Mannose -Acetylneuraminic acid Fucose

10 Unlabeled ULM CA GLYCA-F49 (unlabeled ULM-1008-CA GLYCA-F51 (unlabeled ULM-1005-CA GLYCA-F84 (unlabeled ULM CA GLYCA-F50 (unlabeled ULM CA GLYCA-F (unlabeled ULM CA GLYCA-F59 (unlabeled ULM-101-CA GLYCA-F (unlabeled ULM-1009-CA GLYCA-F7 (unlabeled ULM CA GLYCA-F5 (unlabeled ULM-1007-CA GLYCA-F9 (unlabeled ULM-100-CA GLYCA-F70 (unlabeled ULM-1005-CA GLYCA-F71 (unlabeled 11.0 * Galactose ( 1 C Galactose -Acetylgalactosamine Glucose -Acetylglucosamine Mannose -Acetylneuraminic acid Fucose

11 ULM-1000-CA GLYCA-F7 (unlabeled ULM-1001-CA GLYCA-F75 (unlabeled ULM-1017-CA GLYCA-1 (unlabeled β β ULM-1008-CA GLYCA-F5 (unlabeled ULM-1017-CA GLYCA-F (unlabeled 7 1. ULM CA GLYCA-F54 (unlabeled ULM-1004-CA GLYCA-F7 (unlabeled ULM-100-CA GLYCA-F74 (unlabeled ULM CA GLYCA-55 (unlabeled β β ULM CA GLYCA- (unlabeled β β ULM CA GLYCA- (unlabeled β β ULM-1018-CA GLYCA-7 (unlabeled β β ULM CA GLYCA- (unlabeled β β * Galactose ( 1 C Galactose -Acetylgalactosamine Glucose -Acetylglucosamine Mannose -Acetylneuraminic acid Fucose

12 Unlabeled ULM-1017-CA GLYCA-4 (unlabeled β β ULM CA GLYCA-5 (unlabeled β β ULM CA GLYCA-7 (unlabeled β β ULM CA GLYCA-11 (unlabeled β β ULM CA GLYCA-1 (unlabeled β β * Galactose ( 1 C Galactose -Acetylgalactosamine Glucose -Acetylglucosamine Mannose -Acetylneuraminic acid Fucose

13 Pair ne 4-ITRPHEYL A-D-LACAC Pair Two S LEXLEX Labeled and Unlabeled Pairs ULM-1009-CA GLYCA-F41 (unlabeled CLM CA GLYCA-F47 ULM-1017-CA GLYCA-F (unlabeled CLM-1010-CA GLYCA-F-1C-GAL ULM CA GLYCA-5 (unlabeled β Pair Three GL CLM-1011-CA GLYCA-5-1C-GAL8,8 ([galactose- 1 C, 99%] β β β Pair Four GLACAC ULM CA GLYCA-GLACAC (unlabeled CLM CA GLYCA-F77 (galactose- 1 C Pair Five DL ULM-1015-CA GLYCA-FX (unlabeled CLM CA GLYCA-FX-1C-GAL Pair Six S DIL ULM-101-CA GLYCA-F (unlabeled CLM-1004-CA GLYCA-F-1C-GAL ULM-1017-CA GLYCA-4 (unlabeled β Pair Seven DIL CLM-101-CA GLYCA-4-1C-GAL8,8 ([galactose- 1 C, 99%] β β β ULM CA GLYCA- (unlabeled β Pair Eight L CLM-101-CA GLYCA--1C-GAL, ([galactose- 1 C, 99%] β β β * Galactose ( 1 C Galactose -Acetylgalactosamine Glucose -Acetylglucosamine Mannose -Acetylneuraminic acid Fucose

14 Labeled and Unlabeled Pairs ULM CA GLYCA-11 (unlabeled β β Pair ine LEXLEX CLM CA GLYCA-11-1C-GAL8,8 ([galactose- 1 C, 99%] β β ULM CA GLYCA-7 (unlabeled β Pair Ten S DIL CLM CA GLYCA-7-1C-GAL8,8 ([galactose- 1 C, 99%] β β β ULM CA GLYCA- (unlabeled β Pair Eleven GL CLM-101-CA GLYCA--1C-GAL, ([galactose- 1 C, 99%] β β β Please visit isotope.com for pricing, ordering, and availability of other glycans. Also available: ILIGHT : A Glycan-Tagging Kit for -Linked Glycan Quantification * Galactose ( 1 C Galactose -Acetylgalactosamine Glucose -Acetylglucosamine Mannose -Acetylneuraminic acid Fucose

15 Example Certificate of Analysis (CoA Exclusively distributed by: Cambridge Isotope Laboratories, Inc. 50 Frontage Road Andover, MA (USA (Fax Certificate of Analysis β β Catalog: CLM CA Lot: BT P Synonym: S tril Isotope: ([Galactose- 1 C, 99%] Form: Lyophilized Solid Formula: 1 C 18 C 1 H Mass: 97.1 Unit: 500 pmol (~ 1.9 µg Storage: -0 C, Stable 5 Years Certification Cassia, LLC, guarantees that this material meets or exceeds the specifications stated. Absolute identity, as well as chemical and isotopic impurities, are assured by the use of unambiguous synthetic routes and multiple chemical analyses whenever possible. Quality Control Test Specification Result Appearance of Solid White Powder Conforms HPLC for Chemical Purity 98% Conforms 1 H-MR for Identification and Chemical Purity Conforms ESI-MS for Identification (Mono-Isotopic 94.4 [C 18 1 C 1 H H] 94. [C 18 1 C 1 H H] This Product is for Laboratory Use nly. Cassia, LLC, manufactures highly pure research compounds which are for research applications only not for diagnostic purposes. Persons intending to use these products for other applications do so at their own responsibility and must comply with all appropriate regulations.

16 Enriching Scientific Discovery To request a quotation or place an order, please contact Sales at sales@eurisotop.com Telephone: ( ( Germany & Austria

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