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Merck
CN

938645

Sigma-Aldrich

N6-[[(1α,8α,9α)-Bicyclo[6.1.0]non-4-yn-9-ylmethoxy]carbonyl]-L-lysine

≥95%

Synonym(s):

L-Lysine, N6-[[(1α,8α,9α)-bicyclo[6.1.0]non-4-yn-9-ylmethoxy]carbonyl]-, Nε-(((1R,8S)-Bicyclo[6.1.0]non-4-yn-9-ylmethoxy)carbonyl)-L-lysine

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About This Item

Empirical Formula (Hill Notation):
C17H26N2O4
CAS Number:
1384100-45-1
Molecular Weight:
322.40
MDL number:
MFCD26793798
NACRES:
NA.21

Key Documents

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Quality Level

100

Assay

≥95%

form

powder or crystals

color

white to off-white

storage temp.

2-8°C

SMILES string

C(OC(NCCCC[C@@H](C(O)=O)N)=O)[C@H]1[C@]2([C@@]1(CCC#CCC2)[H])[H]

InChI

InChI=1S/C17H26N2O4/c18-15(16(20)21)9-5-6-10-19-17(22)23-11-14-12-7-3-1-2-4-8-13(12)14/h12-15H,3-11,18H2,(H,19,22)(H,20,21)/t12-,13+,14+,15-/m0/s1

InChI key

QLDVOCPEKYLEOT-YJNKXOJESA-N

Application

N6-[[(1α,8α,9α)-Bicyclo[6.1.0]non-4-yn-9-ylmethoxy]carbonyl]-L-lysine is particularly suited for the labeling and crosslinking of proteins on the surface of live mammalian cells. Its high reactivity and biocompatibility allow for the precise modification of target proteins with minimal off-target effects and without compromising cell viability. This capability is crucial for studying protein dynamics, interactions, and functions in real time, providing insights into cellular processes that were previously unattainable with traditional biochemical methods.

Features and Benefits

N6-[[(1α,8α,9α)-Bicyclo[6.1.0]non-4-yn-9-ylmethoxy]carbonyl]-L-lysine unique structure, offers unparalleled reactivity towards azide-functionalized biomolecules facilitating rapid and specific conjugation reactions without the need for cytotoxic copper catalysts.

Storage Class Code

11 - 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
0000344448

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Genetic Encoding of bicyclononynes and trans-cyclooctenes for site-specific protein labeling in vitro and in live mammalian cells via rapid fluorogenic Diels-Alder reactions
Lang K, et al.
Journal of the American Chemical Society, 134(25), 10317-10320 (2012)
Strain-promoted sydnone bicyclo-[6.1.0]-nonyne cycloaddition?Electronic supplementary information (ESI) available: Full experimental details, 1H/13C NMR spectral data, protein synthesis and purification. See DOI: 10.1039/c3sc53332h
Wallace S, et al.
Chemical Science, 5(5), 1742-1744 (2014)
Kathrin Lang et al.
Journal of the American Chemical Society, 134(25), 10317-10320 (2012-06-15)
Rapid, site-specific labeling of proteins with diverse probes remains an outstanding challenge for chemical biologists. Enzyme-mediated labeling approaches may be rapid but use protein or peptide fusions that introduce perturbations into the protein under study and may limit the sites
Genetic encoding of a bicyclo[6.1.0]nonyne-charged amino acid enables fast cellular protein imaging by metal-free ligation
Borrmann A, et al.
Chembiochem, 13(14), 2094-2095 (2012)
Gong Zhang et al.
ACS central science, 2(5), 325-331 (2016-06-10)
Selective manipulation of protein kinases under living conditions is highly desirable yet extremely challenging, particularly in a gain-of-function fashion. Here we employ our recently developed bioorthogonal cleavage reaction as a general strategy for intracellular activation of individual kinases. Site-specific incorporation

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