D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid

Names

[ Name ]:
D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid

[Synonym ]:
(3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
(3S)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid
(R)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid
3-Isoquinolinecarboxylic acid, 1,2,3,4-tetrahydro-, (3S)-
(3S)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid
MFCD00144038
D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid
H-D-Tic-OH
(R)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid

Biological Activity

[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.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Others

[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.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
372.0±42.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₀H₁₁NO₂

[ Molecular Weight ]:
177.200

[ Flash Point ]:
178.8±27.9 °C

[ Exact Mass ]:
177.078979

[ PSA ]:
49.33000

[ LogP ]:
0.86

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.577

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2933499090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933499090

[ Summary ]:
2933499090. other compounds containing in the structure a quinoline or isoquinoline ring-system (whether or not hydrogenated), not further fused. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Constrained phenylalanine analogues. Preferred conformation of the 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) residue.

Int. J. Pept. Protein Res. 40 , 222, (1992)

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 hel...

T. Mehler et al.

Tetrahedron Asymmetry 5 , 185, (1994)

Related Compounds

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