901991

Dde biotin picolyl azide

Name: Dde biotin picolyl azide
Brand: SIAL

别名:

N-[6-(Azidomethyl)-3-pyridinyl]-5-(4,4-dimethyl-2,6-dioxocyclohexylidene)-25-[(3aS,4S,6aR)-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl]-21-oxo-8,11,14,17-tetraoxa-4,20-diazapentacosanamide

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关于此项目

经验公式（希尔记法）:

C₃₈H₅₇N₉O₉S

化学文摘社编号:

2055048-42-3

分子量:

815.98

MDL number:

MFCD30458027

UNSPSC Code:

12352125

NACRES:

NA.22

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InChI key

CYXSXYDLWXHYSI-JKMQWNNCSA-N

SMILES string

S1[C@@H]([C@@H]4NC(=O)N[C@@H]4C1)CCCCC(=O)NCCOCCOCCOCCOCCC(=C3C(=O)CC(CC3=O)(C)C)NCCC(=O)Nc2cnc(cc2)CN=[N+]=[N-]

form

solid

reaction suitability

reaction type: click chemistry

storage temp.

−20°C

Application

Dde biotin picolyl azide is a unique alkyne-reactive, cleavable biotin probe that allows for release of the captured biomolecules from streptavidin under mild conditions. This reagent contains a biotin moiety linked to a picolyl azide moiety through a spacer arm containing a hydrazine-cleavable Dde moiety. Captured biomolecules can be efficiently released, typically >90% with 2% hydrazine in aqueous media.
Dde biotin picolyl azide incorporates a copper-chelating motif that dramatically accelerates the Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction under conditions relevant to biomolecular labeling. Discovery of azides with an internal Cu(I)-chelating motif greatly enhances the utility of the CuAAC reaction for various applications. Some examples are monitoring the dynamic glycan biosynthesis in living organisms; sensitive detection of metabolically-labeled proteins, DNAs, and RNAs; and many other applications where rate acceleration and reduced cell toxicity are highly desirable.