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

Modify Date: 2024-01-03 17:22:26

D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid Structure
D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid structure
 Common Name D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid
CAS Number 103733-65-9 Molecular Weight 177.200
Density 1.2±0.1 g/cm3 Boiling Point 372.0±42.0 °C at 760 mmHg
Molecular Formula C10H11NO2 Melting Point N/A
MSDS Chinese USA Flash Point 178.8±27.9 °C
Symbol GHS07
GHS07		 Signal Word Warning

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


(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.

 Names

Name (R)-(+)-1,2,3,4-Tetrahydroisoquinoline-3-Carboxylic Acid
Synonym More Synonyms

  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
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
Storage condition 2-8°C

 MSDS

Material Safety Data Sheet
Section1. Identification of the substance
Product Name: D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid
Synonyms:
Section2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
Section3. Composition/information on ingredients.
Ingredient name:D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid
CAS number:103733-65-9
Section4. First aid measures
Skin contact:Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact:Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation:Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion:Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Section5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.
Section6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution:Wear approved mask/respirator
Hand precaution:Wear suitable gloves/gauntlets
Skin protection:Wear suitable protective clothing
Eye protection:Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.
Section7. Handling and storage
Handling:This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:
Section8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.
Section9. Physical and chemical properties
Appearance:Not specified
Boiling point:No data
No data
Melting point:
Flash point:No data
Density:No data
Molecular formula:C10H11NO2
Molecular weight:177.2
Section10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.
Section11. Toxicological information
No data.
Section12. Ecological information
No data.
Section13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.
Section14. Transportation information
Non-harzardous for air and ground transportation.
Section15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

SECTION 16 - ADDITIONAL INFORMATION
N/A

 Safety Information

Symbol GHS07
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

 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...

T. Mehler et al.

Tetrahedron Asymmetry 5 , 185, (1994)

 Synonyms

(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
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Chemsrc provides CAS#:103733-65-9 MSDS, density, melting point, boiling point, structure, etc. Its name is D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid>> amp version: D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid

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