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Key Documents

900893

Sigma-Aldrich

L-Homopropargylglycine hydrochloride

Synonym(s):

HPG

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About This Item

Empirical Formula (Hill Notation):
C6H9NO2 · HCl
CAS Number:
Molecular Weight:
163.60
UNSPSC Code:
12352209
NACRES:
NA.22

form

powder or crystals

availability

available only in USA

mp

162 °C

storage temp.

−20°C

SMILES string

O=C(O[H])[C@@](C([H])([H])C([H])([H])C#C[H])([H])N([H])[H].Cl[H]

InChI

1S/C6H9NO2/c1-2-3-4-5(7)6(8)9/h1,5H,3-4,7H2,(H,8,9)

InChI key

SCGJGNWMYSYORS-UHFFFAOYSA-N

Application

L-Homopropargylglycine (HPG) is an amino acid analog of methionine that contains a very small modification, specifically an alkyne moiety. This compound can be fed to cultured cells and incorporated into proteins during active protein synthesis. Detection utilizes the chemoselective ligation or “click” reaction between an azide and an alkyne or cyclooctyne. For example the alkyne-modified protein can be detected with either fluorescent azide or biotin azide. Detection sensitivity with these reagents in 1-D gels and Western blots is in the low femtomole range and compatible with downstream LC-MS/MS and MALDI-MS analysis.

Pictograms

Flame

Signal Word

Danger

Hazard Statements

Hazard Classifications

Self-react. C

Storage Class Code

5.2 - Organic peroxides and self-reacting hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Cleavable biotin probes for labeling of biomolecules via azide? alkyne cycloaddition.
Szychowski J, et al.
Journal of the American Chemical Society, 132(51), 18351-18360 (2010)
Using Click-Chemistry for Visualizing in Situ Changes of Translational Activity in Planktonic Marine Bacteria.
Leizeaga A, et al.
Frontiers in Microbiology, 8 (2017)
Cell-free production of Gaussia princeps luciferase?antibody fragment bioconjugates for ex vivo detection of tumor cells.
Patel K G, et al.
Biochemical and Biophysical Research Communications, 390(3), 971-976 (2009)
The dynamic shuttling of SIRT1 between cytoplasm and nuclei in bronchial epithelial cells by single and repeated cigarette smoke exposure.
Yanagisawa S, et al.
PLoS ONE, 13(3), e0193921-e0193921 (2018)
Live-cell imaging of alkyne-tagged small biomolecules by stimulated Raman scattering.
Wei L, et al.
Nature Methods, 11(4), 410-410 (2014)

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