L-Azidohomoalanine| CAS# 120042-14-0 | Amino Acid Analog

MedKoo Cat#: 572672 | Name: L-Azidohomoalanine

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

L-Azidohomoalanine is an amino acid analog that provides a fast, sensitive, non-toxic and non-radioactive alternative to the traditional radioactive 35S-methionine for the detection of nascent protein. L-azidohomoalaine contains a small modification and its azido moiety can be fed to cultured cells and incorporated into proteins during active protein synthesis.

Chemical Structure

L-Azidohomoalanine

CAS#120042-14-0 (free base)

Theoretical Analysis

MedKoo Cat#: 572672

Name: L-Azidohomoalanine

CAS#: 120042-14-0 (free base)

Chemical Formula: C4H8N4O2

Exact Mass: 144.0647

Molecular Weight: 144.13

Elemental Analysis: C, 33.33; H, 5.59; N, 38.87; O, 22.20

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 405.00	2 Weeks

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Related CAS #

120042-14-0 (free base) 942518-29-8 (HCl)

Synonym

4-Azido-L-homoalanine; H-γ-Azido-Abu-OH; (S)-2-Amino-4-azidobutanoic Acid

IUPAC/Chemical Name

(S)-2-amino-4-azidobutanoic acid

InChi Key

NNWQLZWAZSJGLY-VKHMYHEASA-N

InChi Code

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

SMILES Code

N[C@@H](CCN=[N+]=[N-])C(O)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

L-Azidohomoalanine is an alkyl chain-based PROTAC linker that can be used in the synthesis of PROTACs.

In vitro activity:

The azide-containing amino-acid derivative enables a highly efficient and specific reaction termed click chemistry, whereby the azide group of the L-AHA (L-azidohomoalanine) reacts with a reactive alkyne derivate, like dibenzocyclooctyne (DBCO) derivatives, using strain-promoted alkyne-azide cycloaddition (SPAAC). This study also describes examples of downstream visualization, affinity purification of L-AHA-labeled proteins and differential expression analysis. Reference: Methods Mol Biol. 2022;2533:229-246. https://pubmed.ncbi.nlm.nih.gov/35796992/

In vivo activity:

To isolate pure axonal mRNA and protein, rat superior cervical ganglion sympathetic neurons were cultured in compartmentalized Campenot chambers. Metabolic labeling of axonally synthesized proteins labeled with the methionine analog, L-azidohomoalanine, showed that TH is locally synthesized in axons. Reference: RNA. 2016 Jun;22(6):883-95. https://pubmed.ncbi.nlm.nih.gov/27095027/

Preparing Stock Solutions

The following data is based on the product molecular weight 144.13 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Kern M, Ferreira-Cerca S. Differential Translation Activity Analysis Using Bioorthogonal Noncanonical Amino Acid Tagging (BONCAT) in Archaea. Methods Mol Biol. 2022;2533:229-246. doi: 10.1007/978-1-0716-2501-9_14. PMID: 35796992; PMCID: PMC9761519. 2. Su T, Wang Z, Zhang Z, Hou Z, Han X, Yang F, Liu H. Resveratrol regulates Hsp60 in HEK 293T cells during activation of SIRT1 revealed by nascent protein labeling strategy. Food Nutr Res. 2022 Apr 21;66. doi: 10.29219/fnr.v66.8224. PMID: 35517847; PMCID: PMC9034730. 3. Gervasi NM, Scott SS, Aschrafi A, Gale J, Vohra SN, MacGibeny MA, Kar AN, Gioio AE, Kaplan BB. The local expression and trafficking of tyrosine hydroxylase mRNA in the axons of sympathetic neurons. RNA. 2016 Jun;22(6):883-95. doi: 10.1261/rna.053272.115. Epub 2016 Apr 19. PMID: 27095027; PMCID: PMC4878614. 4. Zhang J, Wang J, Ng S, Lin Q, Shen HM. Development of a novel method for quantification of autophagic protein degradation by AHA labeling. Autophagy. 2014 May;10(5):901-12. doi: 10.4161/auto.28267. Epub 2014 Mar 24. PMID: 24675368; PMCID: PMC5119066.

In vitro protocol:

In vivo protocol:

1. Gervasi NM, Scott SS, Aschrafi A, Gale J, Vohra SN, MacGibeny MA, Kar AN, Gioio AE, Kaplan BB. The local expression and trafficking of tyrosine hydroxylase mRNA in the axons of sympathetic neurons. RNA. 2016 Jun;22(6):883-95. doi: 10.1261/rna.053272.115. Epub 2016 Apr 19. PMID: 27095027; PMCID: PMC4878614. 2. Zhang J, Wang J, Ng S, Lin Q, Shen HM. Development of a novel method for quantification of autophagic protein degradation by AHA labeling. Autophagy. 2014 May;10(5):901-12. doi: 10.4161/auto.28267. Epub 2014 Mar 24. PMID: 24675368; PMCID: PMC5119066.

1: Wang J, Zhang J, Lee YM, Ng S, Shi Y, Hua ZC, Lin Q, Shen HM. Nonradioactive quantification of autophagic protein degradation with L-azidohomoalanine labeling. Nat Protoc. 2017 Dec;12(2):279-288. doi: 10.1038/nprot.2016.160. Epub 2017 Jan 12. PubMed PMID: 28079880. 2: Roth S, Drewe WC, Thomas NR. A concise and scalable route to L-azidohomoalanine. Nat Protoc. 2010 Dec;5(12):1967-73. doi: 10.1038/nprot.2010.164. Epub 2010 Nov 18. PubMed PMID: 21127494.