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940674

Sigma-Aldrich

DBCO-NHCO-PEG4-amine TFA

new

≥95%

Synonym(s):

15-Amino-N-[3-(11,12-didehydrodibenz[b,f]azocin-5(6H)-yl)-3-oxopropyl]-4,7,10,13-tetraoxapentadecanamide, 4,7,10,13-Tetraoxapentadecanamide, 15-amino-N-[3-(11,12-didehydrodibenz[b,f]azocin-5(6H)-yl)-3-oxopropyl], ADIBO-PEG4-amine TFA

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About This Item

Empirical Formula (Hill Notation):
C29H37N3O6 · xC2HF3O2
CAS Number:
1255942-08-5
Molecular Weight:
523.62 (free base basis)
MDL number:
MFCD28334576

Quality Level

100

Assay

≥95%

form

solid

color

colorless to yellow-brown

storage temp.

−20°C

SMILES string

O=C(NCCC(=O)N1C=2C=CC=CC2C#CC=3C=CC=CC3C1)CCOCCOCCOCCOCCN

InChI

1S/C29H37N3O6.C2HF3O/c30-13-16-36-18-20-38-22-21-37-19-17-35-15-12-28(33)31-14-11-29(34)32-23-26-7-2-1-5-24(26)9-10-25-6-3-4-8-27(25)32;3-2(4,5)1-6/h1-8H,11-23,30H2,(H,31,33);1H

Application

DBCO-PEG4-Amine TFA is a heterobifunctional building block with two reactive terminals. The Dibenzocyclooctyne (DBCO) terminus is useful for copper-free click chemistry. DBCO compounds react with azides without need of Cu(I) catalyst due to the strained nature of alkyne resulting in formation of fast and stable triazole linkage. The amine terminus is useful for reaction with carboxylic acid containing linkers in presence in actiavtors such as EDC or HATU.

Features and Benefits

The PEG4 linker is suited for improving solubility of resulting conjugates and provides sufficient length to minimize interactions between macromolecules of interest.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Click chemistry for the preparation of advanced macromolecular architectures
Akeroyd N, et al.
European Polymer Journal, 47, 1207-1231 (2010)
Pamela V Chang et al.
Proceedings of the National Academy of Sciences of the United States of America, 107(5), 1821-1826 (2010-01-19)
Chemical reactions that enable selective biomolecule labeling in living organisms offer a means to probe biological processes in vivo. Very few reactions possess the requisite bioorthogonality, and, among these, only the Staudinger ligation between azides and triarylphosphines has been employed
A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes.
Vsevolod V Rostovtsev et al.
Angewandte Chemie (International ed. in English), 41(14), 2596-2599 (2002-08-31)

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