Name: Azido-PEG1-methyl ester
Brand: BOC Sciences
Rating: 5 (1 reviews)

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Purity

98%

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Please store the product under the recommended conditions in the Certificate of Analysis.

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IUPACName

methyl 3-(2-azidoethoxy)propanoate

Synonyms

methyl 3-(2-azidoethoxy)propanoate; Propanoic acid, 3-(2-azidoethoxy)-, methyl ester

InChI Key

LAQALTVGFQMCEV-UHFFFAOYSA-N

InChI

InChI=1S/C6H11N3O3/c1-11-6(10)2-4-12-5-3-8-9-7/h2-5H2,1H3

SMILES

COC(=O)CCOCCN=[N+]=[N-]

1. Novel azido fatty acid ester derivatives from conjugated C(18) enynoate

M S Lie Ken Jie, M S Alam Chem Phys Lipids. 2001 May;111(1):29-35.doi: 10.1016/s0009-3084(01)00140-2.

Methyl octadec-11Z-en-9-ynoate (1) was epoxidized to give methyl 11,12-Z-epoxy-octadec-9-ynoate (2, 81%). Acid catalyzed ring opening of the epoxy ring of compound 2 gave methyl 11,12-dihydroxy-octadec-9-ynoate (3, 80%). The latter was treated with mesyl chloride to yield methyl 11,12-dimesyloxy-octadec-9-ynoate (4, 76%). Reaction of compound 4 with sodium azide furnished methyl 11-azido-12-mesyloxy-octadec-9-ynoate (5a, 49%) and methyl 11-azido-octadec-11E-en-9-ynoate (5b, 24%). Compound 2 was semi-hydrogenated over Lindlar catalyst to give methyl 11,12-Z-epoxy-octadec-9Z-enoate (6, 90%). This allylic epoxy fatty ester (6) was reacted with sodium azide to give a mixture of methyl 11-azido-12-hydroxy-octadec-9Z-enoate (7a) and methyl 9-azido-12-hydroxy-octadec-9E-enoate (7b), which could not be separated into individual components by silica chromatography. Chromic acid oxidation of the mixture of compounds 7a and 7b furnished methyl 9-azido-12-oxo-octadec-10E-enoate (8, 42% based on amount of compound 6 used) and an intractable mixture of polar compounds. The various products were characterized by NMR spectroscopic and mass spectral analyses.

Azido-PEG1-methyl ester is a PEG-based azide linker designed for modular PROTAC construction, enabling efficient conjugation of targeting ligands and E3 ligase binders through bioorthogonal “click” chemistry. Its polyethylene glycol segment provides conformational flexibility and improved solubility, while the azide handle supports selective functionalization under mild conditions. This molecule will be described in detail below, including its structural features and practical reactivity considerations for preparing targeted protein degradation tools.

Structure: The linker contains an azide functional group attached to a short polyethylene glycol chain terminated as a methyl ester. It features ether linkages within the PEG segment, an ester carbonyl, and an azide moiety capable of participating in cycloaddition reactions. Overall, it is polar and compatible with aqueous or mixed solvent environments.

Reactivity: Azido-PEG1-methyl ester is primarily used in copper-catalyzed azide–alkyne cycloaddition or related azide-based click strategies to connect PROTAC components bearing a complementary alkyne. Typical preparations employ a compatible Cu(I) catalytic system, appropriate ligands to control copper speciation, and solvents such as aqueous buffers with an organic co-solvent. Reaction progress is commonly monitored by analytical methods, and mild temperatures are selected to preserve sensitive binding motifs.

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It is commonly abbreviated as: C₁V₁ = C₂V₂