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774995

Sigma-Aldrich

N2-[(1,1-Dimethylethoxy)carbonyl]-N6-[(2-propynyloxy)carbonyl]-L-lysine

90%

Synonym(s):

N-α-Boc-propargyl-lysine-OH

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About This Item

Empirical Formula (Hill Notation):
C15H24N2O6
CAS Number:
1202704-91-3
Molecular Weight:
328.36
MDL number:
MFCD22989423
UNSPSC Code:
12352200
PubChem Substance ID:
329767726
NACRES:
NA.22

Assay

90%

form

liquid

reaction suitability

reaction type: click chemistry

refractive index

n20/D 1.475

density

1.167 g/mL at 25 °C

SMILES string

CC(C)(C)OC(=O)N[C@@H](CCCCNC(=O)OCC#C)C(O)=O

InChI

1S/C15H24N2O6/c1-5-10-22-13(20)16-9-7-6-8-11(12(18)19)17-14(21)23-15(2,3)4/h1,11H,6-10H2,2-4H3,(H,16,20)(H,17,21)(H,18,19)/t11-/m0/s1

InChI key

VHCJWKDEXGPNCX-NSHDSACASA-N

Application

Alkyne modified lysine that has been shown to be incorporated site-specifically into recombinant proteins.

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Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Precautionary Statements

P280

Hazard Classifications

Skin Sens. 1

Storage Class Code

10 - Combustible liquids not in Storage Class 3

WGK

WGK 3

Flash Point(F)

164.0 °F

Flash Point(C)

73.33 °C

Certificates of Analysis (COA)

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Duy P Nguyen et al.
Journal of the American Chemical Society, 131(25), 8720-8721 (2009-06-12)
We demonstrate that an orthogonal Methanosarcina barkeri MS pyrrolysyl-tRNA synthetase/tRNA(CUA) pair directs the efficient, site-specific incorporation of N6-[(2-propynyloxy)carbonyl]-L-lysine, containing a carbon-carbon triple bond, and N6-[(2-azidoethoxy)carbonyl]-L-lysine, containing an azido group, into recombinant proteins in Escherichia coli. Proteins containing the alkyne functional
Synthesis of threefold glycosylated proteins using click chemistry and genetically encoded unnatural amino acids.
Emine Kaya et al.
Chembiochem : a European journal of chemical biology, 10(18), 2858-2861 (2009-11-10)

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