D-4-Pyridylalanine

Base Information

• Chemical Name: D-4-Pyridylalanine
• CAS No.: 37535-50-5
• Molecular Formula: C₈H₁₀N₂O₂
• Molecular Weight: 166.18
• Hs Code.: 2933399090
• European Community (EC) Number: 838-336-2
• UNII: DQJ6W06CEK
• DSSTox Substance ID: DTXSID201288560
• Mol file: 37535-50-5.mol

Synonyms:4-Pyridinepropanoicacid, a-amino-, (R)-;3-(4-Pyridyl)-D-alanine;b-4-Pyridyl-D-alanine;

Chemical Property of D-4-Pyridylalanine

Chemical Property:

• Melting Point: 280 °C (decomp)
• Refractive Index: 1.603
• Boiling Point: 346.4 °C at 760 mmHg
• PKA: 1.95±0.10(Predicted)
• Flash Point: 163.3 °C
• PSA: 76.21000
• Density: 1.271 g/cm³
• LogP: 0.73630
• Storage Temp.: Store at 0-5°C
• XLogP3: -2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 166.074227566
• Heavy Atom Count: 12
• Complexity: 155

Purity/Quality:

99% ^*data from raw suppliers

3-(4-Pyridyl)-D-alanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN=CC=C1CC(C(=O)O)N
• Isomeric SMILES: C1=CN=CC=C1C[C@H](C(=O)O)N
• Uses: 3-(4-Pyridyl)-D-alanine is a derivative of alanine (A480995) which is an amino acid that is commonly found in bacteria, such as Streptococcus faecalis. Alanine is essential for the biosynthesis of peptidoglycan crosslinking sub-units that are used for bacterial cell walls. D-Alanine is also known to cause cytotoxic oxidative stress in brain tumour cells.

Technology Process of D-4-Pyridylalanine

There total 2 articles about D-4-Pyridylalanine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

d-methyl 2-acetamido-3-(4-pyridyl)propanoate (131905-74-3,138808-56-7) → (S)-2-amino-3-(pyridin-4-yl)propanoic acid (37535-49-2) + 3-(4-pyridyl)-D-alanine (37535-50-5)

Guidance literature:

With hydrogenchloride; for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Heating;

DOI:10.1021/jo00007a060

Reference yield:

l-methyl 2-acetamido-3-(4-pyridyl)propanoate (131905-73-2,138808-56-7) → (S)-2-amino-3-(pyridin-4-yl)propanoic acid (37535-49-2) + 3-(4-pyridyl)-D-alanine (37535-50-5)

Guidance literature:

With hydrogenchloride; for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Heating;

DOI:10.1021/jo00007a060

Reference yield: 60.0%

4-(diphenylamino)benzaldehyde (4181-05-9) + 3-(4-pyridyl)-D-alanine (37535-50-5) + fullerene-C60 (99685-96-8,161105-99-3,161106-00-9,111138-12-6,133318-63-5,134053-11-5,134931-35-4,134931-36-5,139703-76-7,145633-27-8,175414-73-0,175414-74-1,175414-75-2,175519-12-7,175519-13-8,175519-14-9,175519-15-0,136376-46-0,144906-37-6,144906-38-7,151767-00-9,152882-97-8,152882-98-9,152882-99-0,153062-34-1,154171-74-1,154171-75-2,154333-99-0,154334-00-6,154397-63-4,154460-59-0,199456-56-9,108739-25-9,120329-57-9,120329-58-0) → C86H23N3

Guidance literature:

In toluene; for 18h; Heating;

DOI:10.1016/j.tet.2005.05.112

upstream raw materials:

d-methyl 2-acetamido-3-(4-pyridyl)propanoate

l-methyl 2-acetamido-3-(4-pyridyl)propanoate

Refernces