MedKoo Cat#: 551040 | Name: 4-Azido-L-phenylalanine
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Description:

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

4-Azido-L-phenylalanine, also known as azF, is a genetically-encoded molecular probe. azF is used to study GPCRs in their native cellular environment or under detergent solubilized conditions.

Chemical Structure

4-Azido-L-phenylalanine
4-Azido-L-phenylalanine
CAS# 33173-53-4

Theoretical Analysis

MedKoo Cat#: 551040

Name: 4-Azido-L-phenylalanine

CAS#: 33173-53-4

Chemical Formula: C9H10N4O2

Exact Mass: 206.0804

Molecular Weight: 206.21

Elemental Analysis: C, 52.42; H, 4.89; N, 27.17; O, 15.52

Price and Availability

Size Price Availability Quantity
100mg USD 285.00 2 Weeks
250mg USD 450.00 2 Weeks
500mg USD 750.00 2 Weeks
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Synonym
azF; H-4-Azido-Phe-OH; L-Phe(4-azido)-OH; 4-Azido-L-phenylalanine.
IUPAC/Chemical Name
p-Azido-L-phenylalanine
InChi Key
NEMHIKRLROONTL-QMMMGPOBSA-N
InChi Code
InChI=1S/C9H10N4O2/c10-8(9(14)15)5-6-1-3-7(4-2-6)12-13-11/h1-4,8H,5,10H2,(H,14,15)/t8-/m0/s1
SMILES Code
N[C@@H](CC1=CC=C(N=[N+]=[N-])C=C1)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
>2 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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 206.21 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.

Recalculate based on batch purity %
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
1: Castro A, Rodríguez F, Flórez M, López P, Curotto B, Martínez D, Maturana A, Lardone MC, Palma C, Mericq V, Ebensperger M, Cassorla F. Pseudoautosomal abnormalities in terminal AZFb+c deletions are associated with isochromosomes Yp and may lead to abnormal growth and neuropsychiatric function. Hum Reprod. 2017 Feb;32(2):465-475. doi: 10.1093/humrep/dew333. Epub 2017 Jan 5. PubMed PMID: 28057878. 2: Kon M, Saito K, Mitsui T, Miyado M, Igarashi M, Moriya K, Nonomura K, Shinohara N, Ogata T, Fukami M. Copy Number Variations of the Azoospermia Factor Region and SRY Are Not Associated with the Risk of Hypospadias. Sex Dev. 2016;10(1):12-5. doi: 10.1159/000444938. Epub 2016 Mar 30. PubMed PMID: 27023068. 3: Zhou Y, Ge Y, Xiao L, Guo Q. Rapid and simultaneous screening of 47,XXY and AZF microdeletions by quadruplex real-time polymerase chain reaction. Reprod Biol. 2015 Jun;15(2):113-21. doi: 10.1016/j.repbio.2015.02.002. Epub 2015 Feb 20. PubMed PMID: 26051460. 4: Tian H, Sakmar TP, Huber T. Micelle-Enhanced Bioorthogonal Labeling of Genetically Encoded Azido Groups on the Lipid-Embedded Surface of a GPCR. Chembiochem. 2015 Jun 15;16(9):1314-22. doi: 10.1002/cbic.201500030. Epub 2015 May 11. PubMed PMID: 25962668; PubMed Central PMCID: PMC5287413. 5: Saito K, Miyado M, Kobori Y, Tanaka Y, Ishikawa H, Yoshida A, Katsumi M, Saito H, Kubota T, Okada H, Ogata T, Fukami M. Copy-number variations in Y-chromosomal azoospermia factor regions identified by multiplex ligation-dependent probe amplification. J Hum Genet. 2015 Mar;60(3):127-31. doi: 10.1038/jhg.2014.115. Epub 2015 Jan 8. PubMed PMID: 25566757. 6: Naganathan S, Ray-Saha S, Park M, Tian H, Sakmar TP, Huber T. Multiplex detection of functional G protein-coupled receptors harboring site-specifically modified unnatural amino acids. Biochemistry. 2015 Jan 27;54(3):776-86. doi: 10.1021/bi501267x. Epub 2015 Jan 8. PubMed PMID: 25524496; PubMed Central PMCID: PMC4310623. 7: Tian H, Naganathan S, Kazmi MA, Schwartz TW, Sakmar TP, Huber T. Bioorthogonal fluorescent labeling of functional G-protein-coupled receptors. Chembiochem. 2014 Aug 18;15(12):1820-9. doi: 10.1002/cbic.201402193. Epub 2014 Jul 18. PubMed PMID: 25045132; PubMed Central PMCID: PMC4215543. 8: Zheng HY, Li Y, Shen FJ, Tong YQ. A novel universal multiplex PCR improves detection of AZFc Y-chromosome microdeletions. J Assist Reprod Genet. 2014 May;31(5):613-20. doi: 10.1007/s10815-014-0204-5. Epub 2014 Mar 11. PubMed PMID: 24615019; PubMed Central PMCID: PMC4016378. 9: Yuen RK, Merkoulovitch A, MacDonald JR, Vlasschaert M, Lo K, Grober E, Marshall CR, Jarvi KA, Kolomietz E, Scherer SW. Development of a high-resolution Y-chromosome microarray for improved male infertility diagnosis. Fertil Steril. 2014 Apr;101(4):1079-1085.e3. doi: 10.1016/j.fertnstert.2013.12.027. Epub 2014 Jan 23. PubMed PMID: 24462061. 10: Naganathan S, Grunbeck A, Tian H, Huber T, Sakmar TP. Genetically-encoded molecular probes to study G protein-coupled receptors. J Vis Exp. 2013 Sep 13;(79). doi: 10.3791/50588. PubMed PMID: 24056801; PubMed Central PMCID: PMC3871926. 11: Geng Q, Luo FW, Wu WQ, Xu ZY, Wang L, Wang Q, Xie JS. [Cytogenetic and molecular analysis of idic(Yp) in 1 infertile man and 1 prenatal fetus]. Zhonghua Nan Ke Xue. 2013 Jul;19(7):642-6. Chinese. PubMed PMID: 23926684. 12: Tu XD, Zeng J, Cong XW, Yan AZ, Huang WJ, Lin YH, Zheng DZ, Zhang M, Wang ZH. [Delineation of three structural Y chromosome aberrations combined molecular techniques]. Zhonghua Yi Xue Yi Chuan Xue Za Zhi. 2013 Aug;30(4):420-4. doi: 10.3760/cma.j.issn.1003-9406.2013.04.009. Chinese. PubMed PMID: 23926008. 13: Zhang YS, Dai RL, Wang RX, Zhang ZH, Fadlalla E, Liu RZ. Azoospermia factor microdeletions: occurrence in infertile men with azoospermia and severe oligozoospermia from China. Andrologia. 2014 Jun;46(5):535-40. doi: 10.1111/and.12117. Epub 2013 May 22. PubMed PMID: 23701642. 14: Dai RL, Sun LK, Yang X, Li LL, Zhu HB, Liu RZ. Expansion and de novo occurrence of Y chromosome microdeletions occurring via natural vertical transmission in northeastern China. J Int Med Res. 2012;40(3):1182-91. PubMed PMID: 22906293. 15: Stahl PJ, Mielnik AN, Barbieri CE, Schlegel PN, Paduch DA. Deletion or underexpression of the Y-chromosome genes CDY2 and HSFY is associated with maturation arrest in American men with nonobstructive azoospermia. Asian J Androl. 2012 Sep;14(5):676-82. doi: 10.1038/aja.2012.55. Epub 2012 Jul 23. PubMed PMID: 22820855; PubMed Central PMCID: PMC3734981. 16: Jiang Y, Wang WB, Guo QW, Sha YW, Ouyang HG, Zhou YL. [Multiplex ligation-dependent probe amplification for detecting AZF microdeletions on the Y chromosome in infertile men with azoospermia or severe oligozoospermia]. Zhonghua Nan Ke Xue. 2012 Feb;18(2):115-21. Chinese. PubMed PMID: 22568206. 17: Kozina V, Cappallo-Obermann H, Gromoll J, Spiess AN. A one-step real-time multiplex PCR for screening Y-chromosomal microdeletions without downstream amplicon size analysis. PLoS One. 2011;6(8):e23174. doi: 10.1371/journal.pone.0023174. Epub 2011 Aug 22. PubMed PMID: 21887237; PubMed Central PMCID: PMC3161745. 18: Wu Q, Chen GW, Yan TF, Wang H, Liu YL, Li Z, Duan SW, Sun F, Feng Y, Shi HJ. Prevalent false positives of azoospermia factor a (AZFa) microdeletions caused by single-nucleotide polymorphism rs72609647 in the sY84 screening of male infertility. Asian J Androl. 2011 Nov;13(6):877-80. doi: 10.1038/aja.2011.51. Epub 2011 Jul 18. PubMed PMID: 21765443; PubMed Central PMCID: PMC3739568. 19: Mirfakhraie R, Mirzajani F, Kalantar SM, Montazeri M, Salsabili N, Pourmand GR, Houshmand M. High prevalence of AZFb microdeletion in Iranian patients with idiopathic non-obstructive azoospermia. Indian J Med Res. 2010 Sep;132:265-70. PubMed PMID: 20847372. 20: Plaseski T, Noveski P, Trivodalieva S, Efremov GD, Plaseska-Karanfilska D. Quantitative fluorescent-PCR detection of sex chromosome aneuploidies and AZF deletions/duplications. Genet Test. 2008 Dec;12(4):595-605. doi: 10.1089/gte.2008.0068. PubMed PMID: 19072570.