CAS 103733-65-9|D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid
Introduction：Basic information about CAS 103733-65-9|D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
(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.
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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.
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
InChIKey
BWKMGYQJPOAASG-SECBINFHSA-N
SMILES
O=C(O)C1Cc2ccccc2CN1
Storage condition
2-8°C
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
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%
Articles2
More 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...
