(R)-Aziridine-2-carboxylic acid

Base Information

• Chemical Name: (R)-Aziridine-2-carboxylic acid
• CAS No.: 76314-35-7
• Molecular Formula: C3H5NO2
• Molecular Weight: 87.0782
• DSSTox Substance ID: DTXSID80509465
• Mol file: 76314-35-7.mol

Synonyms:(R)-Aziridine-2-carboxylic acid;76314-35-7;(2R)-Aziridine-2-carboxylic acid;r-aziridine-2-carboxylic;(R)-Aziridine-2-carboxylicacid;DTXSID80509465;AKOS006328972

Chemical Property of (R)-Aziridine-2-carboxylic acid

Chemical Property:

• XLogP3: -3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 87.032028402
• Heavy Atom Count: 6
• Complexity: 80.9

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(N1)C(=O)O
• Isomeric SMILES: C1[C@@H](N1)C(=O)O

Technology Process of (R)-Aziridine-2-carboxylic acid

There total 1 articles about (R)-Aziridine-2-carboxylic acid 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:

methyl 1-acetylaziridine-2-carboxylate (123557-03-9,151910-15-5) → (2R)-2-aziridinecarboxylic acid (76314-35-7) + methyl (2S)-(-)-1-acetylaziridine-2-carboxylate (151910-16-6)

Guidance literature:

With sodium chloride; In water; for 4h; Product distribution; Ambient temperature; Candida cylindracea lipase, potassium phosphate buffer (pH 7.5); Candida cyligracea lipase-catalysed hydrolysis of methyl aziridine-2-carboxylates and 2,3-dicarboxylates; enzymatic resolution; conversion, enantioselectivity, enantiomeric excess;

Reference yield: 24.2%

D-cysteine (921-01-7) + (2R)-2-aziridinecarboxylic acid (76314-35-7) → (2S)-2-amino-3-<(2-amino-1-carboxyethyl)-thio>propanoic acid (114502-00-0) + lanthionine (922-55-4,922-56-5,3183-08-2,5965-92-4,496-98-0)

Guidance literature:

With phosphate buffer; at 37 ℃; for 20h; pH 8.0;

DOI:10.1016/S0040-4020(01)81670-7

Reference yield:

L-Cysteine (52-90-4) + (2R)-2-aziridinecarboxylic acid (76314-35-7) → 3-Amino-2-((R)-2-amino-2-carboxy-ethylsulfanyl)-propionic acid (114501-98-3) + L,L-Lanthionine (733035-13-7,496-98-0)

Guidance literature:

With phosphate buffer; at 37 ℃; for 20h; Yield given. Yields of byproduct given; pH 8.0;

DOI:10.1016/S0040-4020(01)81670-7

upstream raw materials:

methyl 1-acetylaziridine-2-carboxylate

Downstream raw materials:

(2S)-2-amino-3-<(2-amino-1-carboxyethyl)-thio>propanoic acid

lanthionine

3-Amino-2-((R)-2-amino-2-carboxy-ethylsulfanyl)-propionic acid

L,L-Lanthionine

Refernces