Glucose with a reactive thiol group
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Product Categories

Product Type

Biochemicals

Research Area

Endocrinology & Metabolism
Carbohydrate Metabolism

Application

1-thio-β-D-Glucose (sodium salt)

Item No. 16485

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-thio-β-D-glucopyranose, monosodium salt
CAS Number
10593-29-0
Molecular Formula
C6H11O5S • Na
Formula Weight
218.2
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 10 mg/mlPBS (pH 7.2): 10 mg/ml
SMILES
O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1[S-].[Na+]
InChi Code
InChI=1S/C6H12O5S.Na/c7-1-2-3(8)4(9)5(10)6(12)11-2;/h2-10,12H,1H2;/q;+1/p-1/t2-,3-,4+,5-,6+;/m1./s1
InChi Key
VKPBZIVFRYLHPT-WNFIKIDCSA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    250 mg

    $44

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    500 mg

    $71

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    1 g

    $131

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    Product Description

    1-thio-β-D-Glucose is an analog of β-D-glucose in which sulfur replaces the hydroxyl group at the one position. The thiol group allows diverse chemical reactions, including the thiol-Michael addition reaction and polymerization.1,2,3 1-thio-β-D-Glucose can be labeled with technetium-99m for analytical and diagnostic procedures.4,5,6 It can also be used as a substrate for glucose oxidase, which leads to the production of 1-thio-β-D-gluconic acid.7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nair, D.P., Podgórski, M., Chatani, S., et al. The thiol-Michael addition click chemistry reaction: A powerful and widely used tool in materials chemistry. Chem. Mater. 26, 724-744 (2014).

    2. Babiuch, K., Pretzel, D., Tolstik, T., et al. Uptake of well-defined, highly glycosylated, pentafluorostyrene-based polymers and nanoparticles by human hepatocellular carcinoma cells. Macromol. Biosci. 12(9), 1190-1199 (2012).

    3. Watanabe, S., Yoshida, K., Shinkawa, K., et al. Thioglucose-stabilized gold nanoparticles as a novel platform for colorimetric bioassay based on nanoparticle aggregation. Colloids Surf. B Biointerfaces 81(2), 570-577 (2010).

    4. Jun Oh, S., Ryu, J.S., Yoon, E.J., et al. 99mTc-labeled 1-thio-β-D-glucose as a new tumor-seeking agent: Synthesis and tumor cell uptake assay. Appl. Radiat. Isot. 64(2), 207-215 (2006).

    5. Brasileiro, C.B., Pacheco, C.M., Queiroz-Junior, C.M., et al. 99mTc-labeled-1-thio-β-d-glucose as a new tool to temporomandibular joint inflammatory disorders diagnosis. Appl. Radiat. Isot. 68(12), 2261-2267 (2010).

    6. Seidensticker, M., Ulrich, G., Muehlberg, F.L., et al. Tumor cell uptake of 99mTc-Labeled 1-thio-β-D-glucose and 5-thio-ᴅ-glucose in comparison with 2-deoxy-2-[18F]fluoro-ᴅ-glucose in vitro: Kinetics, dependencies, blockage and cell compartment of accumulation. Mol. Imaging Biol. 16(2), 189-198 (2014).

    7. Saa, L., and Pavlov, V. Enzymatic growth of quantum dots: Applications to probe glucose oxidase and horseradish peroxidase and sense glucose. Small 8(22), 3449-3455 (2012).