Cyanotryptophan

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

MedKoo CAT#: 465922

CAS#: 1132749-42-8

Description: Cyanotryptophan is a blue fluorescent amino acid, exhibiting blue fluorescence (λmax ~ 405 nm) with a high quantum yield and long lifetime.

Chemical Structure

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Cyanotryptophan
CAS# 1132749-42-8
Instruction

Theoretical Analysis

MedKoo Cat#: 465922
Name: Cyanotryptophan
CAS#: 1132749-42-8
Chemical Formula: C12H11N3O2
Exact Mass: 229.09
Molecular Weight: 229.239
Elemental Analysis: C, 62.87; H, 4.84; N, 18.33; O, 13.96

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Cyanotryptophan; 4-CN-Trp; 4CNTrp; 4 CN Trp;

IUPAC/Chemical Name: (R)-2-amino-3-(4-cyano-1H-indol-3-yl)propanoic acid

InChi Key: UOPSYGYZOBPCLD-SECBINFHSA-N

InChi Code: InChI=1S/C12H11N3O2/c13-5-7-2-1-3-10-11(7)8(6-15-10)4-9(14)12(16)17/h1-3,6,9,15H,4,14H2,(H,16,17)/t9-/m1/s1

SMILES Code: N[C@H](CC1=CNC2=C1C(C#N)=CC=C2)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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 229.24 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Wu Y, Bertran MT, Rowley J, Calder EDD, Joshi D, Walport LJ. Fluorescent Amino Acid Initiated de novo Cyclic Peptides for the Label-Free Assessment of Cell Permeability*. ChemMedChem. 2021 Oct 15;16(20):3185-3188. doi: 10.1002/cmdc.202100315. Epub 2021 Jul 28. PMID: 34236771; PMCID: PMC8597039.


2: Fong KP, Ahmed IA, Mravic M, Jo H, Kim OV, Litvinov RI, Weisel JW, DeGrado WF, Gai F, Bennett JS. Visualization of Platelet Integrins via Two-Photon Microscopy Using Anti-transmembrane Domain Peptides Containing a Blue Fluorescent Amino Acid. Biochemistry. 2021 Jun 1;60(21):1722-1730. doi: 10.1021/acs.biochem.1c00238. Epub 2021 May 19. PMID: 34010565.


3: Micikas R, Acharyya A, Gai F, Smith AB 3rd. A Scalable Synthesis of the Blue Fluorescent Amino Acid 4-Cyanotryptophan and the Fmoc Derivative: Utility Demonstrated with the Influenza M2 Peptide Tetramer. Org Lett. 2021 Feb 19;23(4):1247-1250. doi: 10.1021/acs.orglett.0c04055. Epub 2021 Feb 3. PMID: 33534596.


4: Acharyya A, Ahmed IA, Gai F. 4-Cyanoindole-based fluorophores for biological spectroscopy and microscopy. Methods Enzymol. 2020;639:191-215. doi: 10.1016/bs.mie.2020.04.014. Epub 2020 Apr 30. PMID: 32475401.


5: Ahmed IA , Rodgers JM , Eng C , Troxler T , Gai F . PET and FRET utility of an amino acid pair: tryptophan and 4-cyanotryptophan. Phys Chem Chem Phys. 2019 Jun 28;21(24):12843-12849. doi: 10.1039/c9cp02126d. Epub 2019 Jun 10. PMID: 31179453; PMCID: PMC6587589.


6: Zhang K , Ahmed IA , Kratochvil HT , DeGrado WF , Gai F , Jo H . Synthesis and application of the blue fluorescent amino acid l-4-cyanotryptophan to assess peptide-membrane interactions. Chem Commun (Camb). 2019 Apr 25;55(35):5095-5098. doi: 10.1039/c9cc01152h. PMID: 30957824; PMCID: PMC6508085.


7: van Wilderen LJGW , Brunst H , Gustmann H , Wachtveitl J , Broos J , Bredenbeck J . Cyano-tryptophans as dual infrared and fluorescence spectroscopic labels to assess structural dynamics in proteins. Phys Chem Chem Phys. 2018 Aug 1;20(30):19906-19915. doi: 10.1039/c8cp00846a. PMID: 30019716.


8: Boville CE, Romney DK, Almhjell PJ, Sieben M, Arnold FH. Improved Synthesis of 4-Cyanotryptophan and Other Tryptophan Analogues in Aqueous Solvent Using Variants of TrpB from Thermotoga maritima. J Org Chem. 2018 Jul 20;83(14):7447-7452. doi: 10.1021/acs.joc.8b00517. Epub 2018 Apr 27. PMID: 29651849; PMCID: PMC6054569.


9: Hilaire MR, Mukherjee D, Troxler T, Gai F. Solvent Dependence of Cyanoindole Fluorescence Lifetime. Chem Phys Lett. 2017 Oct 1;685:133-138. doi: 10.1016/j.cplett.2017.07.038. Epub 2017 Jul 18. PMID: 29225366; PMCID: PMC5720157.


10: Hilaire MR, Ahmed IA, Lin CW, Jo H, DeGrado WF, Gai F. Blue fluorescent amino acid for biological spectroscopy and microscopy. Proc Natl Acad Sci U S A. 2017 Jun 6;114(23):6005-6009. doi: 10.1073/pnas.1705586114. Epub 2017 May 22. PMID: 28533371; PMCID: PMC5468623.