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Merck
CN

742783

Sigma-Aldrich

N-[(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethyloxycarbonyl]-N′-biotinyl-1,8-diamino-3,6-dioxaoctane

for Copper-free Click Chemistry

Synonym(s):

(1α,8α,9β)-Bicyclo[6.1.0]non-4-yn-9-ylmethyl N-{2-{2-{{5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno [3,4-d]imidazol-4-yl]pentanamido}ethoxy}ethoxy}ethyl}carbamate, BCN-biotin

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About This Item

Empirical Formula (Hill Notation):
C27H42N4O6S
CAS Number:
1393600-24-2
Molecular Weight:
550.71
MDL number:
MFCD22549356
UNSPSC Code:
12352200
PubChem Substance ID:
329765590

Key Documents

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reaction suitability

reaction type: click chemistry

storage temp.

−20°C

SMILES string

O=C(CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@H]12)NCCOCCOCCNC(=O)OCC3[C@@H]4CCC#CCC[C@H]34

InChI

1S/C27H42N4O6S/c32-24(10-6-5-9-23-25-22(18-38-23)30-26(33)31-25)28-11-13-35-15-16-36-14-12-29-27(34)37-17-21-19-7-3-1-2-4-8-20(19)21/h19-23,25H,3-18H2,(H,28,32)(H,29,34)(H2,30,31,33)/t19-,20+,21-,22-,23-,25-/m0/s1

InChI key

ZYDQEEHFKLOZCS-SSNODSCZSA-N

Application

Cyclooctyne derivative conjugated to biotin. Useful as a biotinylation reagent for labeling azide containing molecules or compounds. Cyclooctynes are useful in strain-promoted copper-free azide-alkyne cycloaddition reactions. This strained cyclooctyne will react with azide-functionalized compounds without the need for a copper catalyst to result in a stable triazole linkage. Subsequent labeled molecules can be purified using streptavidin or avidin affinity reagents.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBJ0790V
BCBM9971V
BCBM6467V
BCBK7733V
BCBJ0790

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Readily accessible bicyclononynes for bioorthogonal labeling and three-dimensional imaging of living cells.
Jan Dommerholt et al.
Angewandte Chemie (International ed. in English), 49(49), 9422-9425 (2010-09-22)

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