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(R)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid CAS: 103733-65-9

Category: Inhibitors
Product Name: (R)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid
Cat No: I000220
CAS No: 103733-65-9
Molecular Formula: C10H11NO2
Molecular Weight: 177.2
Solubility: 10 mM in DMSO, H2O: < 6.2 mg/mL
CAS 103733-65-9,(R)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid
  • 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.

  • References


[1]. Valle G, et al. Constrained phenylalanine analogues. Preferred conformation of the 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) residue. Int J Pept Protein Res. 1992 Sep-Oct;40(3-4):222-32.


price inquiry for CAS:103733-65-9, Product:(R)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid