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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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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)
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

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