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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: 99.28%
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.
Shipping

Room temperature in continental US; may vary elsewhere.

Storage
Powder -20°C 3 years
4°C 2 years
In solvent -80°C 6 months
-20°C 1 month
Solvent & Solubility
In Vitro: 

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

DMSO : < 1 mg/mL (ultrasonic;warming;heat to 60°C) (insoluble or slightly soluble)

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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
10 mM --- --- ---
*Please refer to the solubility information to select the appropriate solvent.
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Product Name:
(R)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid
Cat. No.:
HY-13987
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