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  3. (R)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid

(R)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid  (Synonyms: D-phenylalanine analogue)

Cat. No.: HY-13987 Purity: ≥98.0%
COA Handling Instructions

(R)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid is a constrained Phe analogue which can fold into a beta-bend and a helical structure, and to adopt a preferred side-chain disposition in the peptide.

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(R)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid Chemical Structure

(R)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid Chemical Structure

CAS No. : 103733-65-9

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Description

(R)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid is a constrained Phe analogue which can fold into a beta-bend and a helical structure, and to adopt a preferred side-chain disposition in the peptide. IC50 value: Target: Three Tic-containing (Tic = 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid) model peptides were synthesized to assess the tendency of this constrained Phe analogue to fold into a beta-bend and a helical structure, and to adopt a preferred side-chain disposition. The results of the solution conformational analysis, performed by using Fourier transform infrared absorption and 1H nuclear magnetic resonance, indicate that in chloroform the -Aib-D-Tic-Aib-, -(Aib)2-D-Tic-(Aib)2-, and -L-Pro-D-Tic- sequences fold into intramolecularly H-bonded forms to a great extent. An X-ray diffraction analysis on p-BrBz-(Aib)2-DL-Tic-(Aib)2-OMe monohydrate and p-BrBz-L-Pro-D-Tic-NHMe allows us to conclude that, while the pentapeptide methylester forms an incipient (distorted) 3(10)-helix, the dipeptide methylamide adopts a type-II beta-bend conformation. In both cases, the D-Tic side-chain conformation is D, gauche(-). The implications for the use of the Tic residue in designing conformationally restricted analogues of bioactive peptides are briefly discussed.

Molecular Weight

177.20

Formula

C10H11NO2

CAS No.
Appearance

Solid

Color

White to off-white

SMILES

O=C([C@@H]1NCC2=C(C=CC=C2)C1)O

Shipping

Room temperature in continental US; may vary elsewhere.

Storage
Powder -20°C 3 years
4°C 2 years
In solvent -80°C 2 years
-20°C 1 year
Solvent & Solubility
In Vitro: 

H2O : 1 mg/mL (5.64 mM; ultrasonic and warming and heat to 60°C)

DMSO : < 1 mg/mL (insoluble or slightly soluble)

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 5.6433 mL 28.2167 mL 56.4334 mL
5 mM 1.1287 mL 5.6433 mL 11.2867 mL
View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

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This equation is commonly abbreviated as: C1V1 = C2V2

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The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only.If necessary, please contact MedChemExpress (MCE).
Purity & Documentation
References

Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.

Optional Solvent Concentration Solvent Mass 1 mg 5 mg 10 mg 25 mg
H2O 1 mM 5.6433 mL 28.2167 mL 56.4334 mL 141.0835 mL
5 mM 1.1287 mL 5.6433 mL 11.2867 mL 28.2167 mL

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

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(R)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid Related Classifications

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    Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

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Product Name:
(R)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid
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HY-13987
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