37535-52-7

Basic information

• Product Name: 3-(2-Pyridyl)-D-alanine
• Synonyms: (R)-2-PYRIDYLALANINE;(R)-2-AMINO-3-PYRIDIN-2-YL-PROPIONIC ACID;(R)-2-AMINO-3-(2'-PYRIDYL)PROPANOIC ACID;(R)-2-AMINO-3-(2-PYRIDYL)PROPIONIC ACID;RARECHEM BK PT 0230;2'-AZA-D-PHENYLALANINE;2'-PYRIDYL-D-ALA;3-(2'-PYRIDYL)-D-ALANINE
• CAS NO: 37535-52-7
• Molecular Formula: C8H10N2O2
• Molecular Weight: 166.18
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;chiral;Alanine [Ala, A];Unusual Amino Acids;a-amino
• Mol File: 37535-52-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 322.4 °C at 760 mmHg
• Flash Point: 148.8 °C
• Appearance: /Solid
• Density: 1.271 g/cm³
• Storage Temp.: -15°C
• PKA: 1.73±0.10(Predicted)
• BRN: 6478361
• CAS DataBase Reference: 3-(2-Pyridyl)-D-alanine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-Pyridyl)-D-alanine(37535-52-7)
• EPA Substance Registry System: 3-(2-Pyridyl)-D-alanine(37535-52-7)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 37535-52-7(Hazardous Substances Data)

Usage

Description

3-(2-Pyridyl)-D-alanine, also known as (αR)-α-amino-2-pyridinepropanoic acid, is a white to off-white powder with unique chemical properties. It is a crucial starting material in the synthesis of various compounds, particularly those with potential pharmaceutical applications.

Uses

Used in Pharmaceutical Industry:
3-(2-Pyridyl)-D-alanine is used as a starting material for the synthesis of imidazole-containing benzodiazepines and their analogs. These compounds serve as inhibitors of farnesyl protein transferase, an enzyme involved in the post-translational modification of proteins, which is a potential target for therapeutic intervention in various diseases.
Used in Research and Development:
In the field of research and development, 3-(2-Pyridyl)-D-alanine is utilized for the creation of novel compounds with potential applications in drug discovery. Its unique structure allows for the exploration of new chemical pathways and the development of innovative therapeutic agents.
Used in Chemical Synthesis:
3-(2-Pyridyl)-D-alanine is also employed in chemical synthesis processes, where it can be used to produce a variety of complex molecules with specific properties. Its versatility as a building block makes it valuable in the development of new materials and compounds for various applications.

Upstream product

• 54495-51-1 (E)-3-(2-pyridyl)acrylic acid 
• 1121-60-4 pyridine-2-carbaldehyde 
• 37535-51-6 (S)-2-amino-3-(pyridin-2-yl)propanoic acid 
• 74164-26-4 N^α-acetyl-β-(2-pyridyl)-L-alanine 
• 19814-60-9 diethyl 2-acetamido-2-(methylpyridin-2-yl)malonate 
• 185379-37-7 N^α-acetyl-β-(2-pyridyl)-DL-alanine ethyl ester 
• 71239-85-5 N-(t-butoxycarbonyl)-3-(pyridin-2-yl)-DL-alanine 

Downstream Products

• 123760-87-2 3-Pyridin-2-yl-2-(3-trifluoromethyl-benzylamino)-propionic acid 
• 79601-06-2 2-(4-Chloro-benzylamino)-3-pyridin-2-yl-propionic acid 
• 123760-86-1 2-(4-Bromo-benzylamino)-3-pyridin-2-yl-propionic acid 
• 17407-44-2 D,L-β-(2-pyridyl)-α-alanine 

Relevant articles and documents

A practical and scalable system for heteroaryl amino acid synthesis

A robust system for the preparation of β-heteroaryl α-amino acid derivatives has been developed using photoredox catalysis. This system operates via regiospecific activation of halogenated pyridines (or other heterocycles) and conjugate addition to dehydroalanine derivatives to deliver a wide range of unnatural amino acids. This process was conducted with good efficiency on large scale, the application of these conditions to amino ketone synthesis is shown, and a simple protocol is given for the preparation of enantioenriched amino acid synthesis, from a number of radical precursors.

Novel preparation of chiral α-amino acids using the Mitsunobu-Tsunoda reaction

An efficient synthesis of racemic or optically active α-amino acids by modified-Mitsunobu alkylation of a racemic or chiral glycine template from alcohols was developed. Libraries of amino acids were prepared in moderate to good yield with good to high enantioselectivity. This simple method widens the scope for preparation of structurally diverse amino acids.

Studies on polypeptides XXXII. Solid-phase synthesis of RNase S-peptide 1-14 analogues; replacement of histidine-12 by β-(2-pyridyl)-L-alanine and β-(4-pyridyl)-L-alanine

The synthesis of two analogues of the N-terminal tetradecapeptide of ribonuclease A (RNase S-peptide 1-14), in which the active site histidine-12 residue is replaced by β-(2-pyridyl)-L-alanine and β-(4-pyridyl)-L-alanine, has been accomplished by the solid-phase method.The enantiomers of β-(2-pyridyl)alanine were obtained by chymotryptic hydrolysis of its racemic Nα-acetyl ethyl ester.The Boc derivative of both L-amino acids has been synthesized.