6-O-2-Propyn-1-yl-D-galactose - CAS 881895-59-6

6-O-2-Propyn-1-yl-D-galactose - CAS 881895-59-6 Catalog number: BADC-00703

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6-O-2-Propyn-1-yl-D-galactose is a nonclaevable glycolinker for the functionalization of cytotoxic drugs and applications in antibody-drug conjugation.

Category
ADCs Linker
Product Name
6-O-2-Propyn-1-yl-D-galactose
CAS
881895-59-6
Catalog Number
BADC-00703
Molecular Formula
C9H14O6
Molecular Weight
218.2
6-O-2-Propyn-1-yl-D-galactose

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Description
6-O-2-Propyn-1-yl-D-galactose is a nonclaevable glycolinker for the functionalization of cytotoxic drugs and applications in antibody-drug conjugation.
Synonyms
6-O-2-Propyn-1-yl-D-galactose
IUPAC Name
2,3,4,5-tetrahydroxy-6-prop-2-ynoxyhexanal
Canonical SMILES
O=C[C@@H]([C@H]([C@H]([C@@H](COCC#C)O)O)O)O
InChI
InChI=1S/C9H14O6/c1-2-3-15-5-7(12)9(14)8(13)6(11)4-10/h1,4,6-9,11-14H,3,5H2
InChIKey
ITQZDWPQQZDNAZ-UHFFFAOYSA-N
Shipping
Room temperature, or blue ice upon request.

6-O-2-Propyn-1-yl-D-galactose is a synthetic carbohydrate derivative with several specialized applications in bioscience. Here are some key applications of 6-O-2-Propyn-1-yl-D-galactose:

Glycobiology Research: This compound is often used in glycobiology to study carbohydrate-protein interactions. By incorporating 6-O-2-Propyn-1-yl-D-galactose into glycan structures, researchers can track and characterize glycosylation patterns on proteins. This assists in understanding how glycosylation affects protein function, stability, and cell signaling.

Metabolic Labeling: 6-O-2-Propyn-1-yl-D-galactose can be employed in metabolic labeling experiments to tag and visualize glycoproteins and glycolipids in cells. When introduced into cellular systems, this sugar analog integrates into glycosylation pathways, allowing for subsequent detection and imaging. This method is pivotal for mapping the spatial and temporal dynamics of glycosylated molecules.

Chemical Biology: In chemical biology, 6-O-2-Propyn-1-yl-D-galactose is used for bioorthogonal chemistry applications such as click chemistry. Its alkyne group allows for specific and efficient labeling reactions, facilitating the conjugation of probes or other functional groups. This enables detailed studies of molecular interactions and the creation of complex biomolecular assemblies.

Drug Delivery Systems: This carbohydrate derivative can be utilized in the design of targeted drug delivery systems. By attaching 6-O-2-Propyn-1-yl-D-galactose to therapeutic agents, researchers can exploit specific carbohydrate-recognition mechanisms to direct drugs to particular cells or tissues. This approach aims to enhance the efficacy and reduce the side effects of treatments.

1.Introducing Glycolinkers for the Functionalization of Cytotoxic Drugs and Applications in Antibody-Drug Conjugation Chemistry
Ekholm FS, Pynnönen H, Vilkman A, Pitkänen V, Helin J, Saarinen J, Satomaa T
Antibody-drug conjugates (ADCs) are promising alternatives to naked antibodies for selective drug-delivery applications and treatment of diseases such as cancer. Construction of ADCs relies upon site-selective, efficient and mild conjugation technologies. The choice of a chemical linker is especially important, as it affects the overall properties of the ADC. We envisioned that hydrophilic bifunctional chemical linkers based on carbohydrates would be a useful class of derivatization agents for the construction of linker-drug conjugates and ADCs. Herein we describe the synthesis of carbohydrate-based derivatization agents, glycolinker-drug conjugates featuring the tubulin inhibitor monomethyl auristatin E and an ADC based on an anti-EGFR antibody. In addition, an initial in vitro cytotoxicity evaluation of the individual components and the ADC is provided against EGFR-positive cancer cells.
The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

Historical Records: 6-O-2-Propyn-1-yl-D-galactose
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