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Sigma-Aldrich

L-Azidohomoalanine hydrochloride

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Synonym(s):
AHA
Empirical Formula (Hill Notation):
C4H8N4O2 · HCl
CAS Number:
Molecular Weight:
180.59

form

powder or crystals

Quality Level

reaction suitability

reaction type: click chemistry

mp

139 °C

storage temp.

−20°C

InChI

1S/C4H8N4O2.ClH/c5-3(4(9)10)1-2-7-8-6;/h3H,1-2,5H2,(H,9,10);1H/t3-;/m0./s1

InChI key

MHHYJRIDKLZZEO-DFWYDOINSA-N

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This Item
81956L1002P17202
mp

139 °C

mp

-

mp

151-153 °C (lit.)

mp

158-162 °C (lit.)

storage temp.

−20°C

storage temp.

-

storage temp.

-

storage temp.

-

Quality Level

100

Quality Level

-

Quality Level

-

Quality Level

-

reaction suitability

reaction type: click chemistry

reaction suitability

reaction type: solution phase peptide synthesis

reaction suitability

reaction type: solution phase peptide synthesis

reaction suitability

reaction type: solution phase peptide synthesis

Application

L-Azidohomoalanine (AHA) is an amino acid analog of methionine that contains a very small modification, specifically an azido 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 azido-modified protein can be detected with either fluorescent alkyne or biotin alkyne. 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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Expanding the diversity of chemical protein modification allows post-translational mimicry.
van Kasteren S I, et al.
Nature, 446(7139), 1105-1105 (2007)
Miao Chen et al.
PLoS genetics, 17(11), e1009899-e1009899 (2021-11-19)
The robust proliferation of cancer cells requires vastly elevated levels of protein synthesis, which relies on a steady supply of aminoacylated tRNAs. Delivery of tRNAs to the cytoplasm is a highly regulated process, but the machinery for tRNA nuclear export
Teresa Rayon et al.
Science (New York, N.Y.), 369(6510) (2020-09-19)
Although many molecular mechanisms controlling developmental processes are evolutionarily conserved, the speed at which the embryo develops can vary substantially between species. For example, the same genetic program, comprising sequential changes in transcriptional states, governs the differentiation of motor neurons

Articles

Drug discovery process by utilizing chemistry reaction of Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition of terminal alkynes with organoazides to yield 1,4-disubstituted 1,2,3-triazoles.

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