Glycine-2-13C

Base Information

• Chemical Name: Glycine-2-13C
• CAS No.: 20220-62-6
• Molecular Formula: C2H5NO2
• Molecular Weight: 76.08
• DSSTox Substance ID: DTXSID70455265
• Nikkaji Number: J814.650K
• Wikidata: Q82277190
• Mol file: 20220-62-6.mol

Synonyms:Glycine-2-13C;20220-62-6;glycine-13c;Glycine 13C;(2-13C)Glycine;DTXSID70455265;HY-Y0966S2;AKOS015913397;CS-T-55424;Glycine-2-13C, 99 atom % 13C;CS-0375783

Chemical Property of Glycine-2-13C

Chemical Property:

• Melting Point: 240 °C (dec.)(lit.)
• PSA: 63.32000
• LogP: -0.27000
• Storage Temp.: Refrigerator
• Solubility.: Water (Slightly)
• XLogP3: -3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 76.035383238
• Heavy Atom Count: 5
• Complexity: 42.9

Purity/Quality:

95% ^*data from raw suppliers

Glycine-13C ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C(=O)O)N
• Isomeric SMILES: [13CH2](C(=O)O)N
• Uses: Labelled analogue of Glycine (G615990), a non-essential amino acid for human development. Glycine (G615990) is an inhibitory neurotransmitter in spinal cord, allosteric regulator of NMDA receptors.

Technology Process of Glycine-2-13C

There total 1 articles about Glycine-2-13C 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:

(2-13C)bromoacetic acid (64891-77-6) → 2-(13)C-glycine (20220-62-6)

Guidance literature:

With ammonium hydroxide; K_. Bloch, J_. Biol_. Chem_., 1949, 179, 1245;

Reference yield: 99.0%

ethanol (64-17-5) + 2-(13)C-glycine (20220-62-6) → ethyl 2-(13)C-glycine hydrochloride (58420-91-0)

Guidance literature:

ethanol; 2-⁽¹³⁾C-glycine; With thionyl chloride; at 20 ℃; for 12.5h; Cooling;

With hydrogenchloride;

DOI:10.1007/s00726-010-0808-8

Reference yield: 95.0%

thionyl chloride (7719-09-7) + 2-(13)C-glycine (20220-62-6) → ethyl 2-(13)C-glycine hydrochloride (58420-91-0)

Guidance literature:

In ethanol; for 2h; Reflux;

DOI:10.1021/om400735p

upstream raw materials:

(2-13C)bromoacetic acid

Downstream raw materials:

ethyl 2-(13)C-glycine hydrochloride

<2-¹³C>Hippuric acid

(C₆H₅C(N⁽¹³⁾CH₂COO)C₆H₄NC(O)C₄NH₇CH₂C₆H₅)Ni

(2-^13C, 2, 3, 3-²H3)-L-tryptophan

Refernces

Assymetric synthesis of (2S,3R)- and (2S,3S)-[2-¹³C;3-²H] glutamic acid

10.1016/j.tetlet.2009.01.062

The research aims to develop a synthetic route for these specific isotopically labeled glutamic acids with high enantioselectivity for metabolic analysis. The study employs key chemicals such as [2-13C] glycine, β-alanine, lithium aluminum deuteride (LiAlD4), and the (S,S)-Et-DuPHOS-Rh catalyst. The synthesis involves the preparation of a stable isotope-labeled dehydroornithine derivative through the Horner–Wadsworth–Emmons reaction, followed by asymmetric hydrogenation or deuteration using the (S,S)-Et-DuPHOS-Rh catalyst. Ruthenium-catalyzed oxidation is then used to convert the intermediate to the target glutamic acids. The enantiopurity of the final products is confirmed to be 99% ee by HPLC analysis. The research concludes that the asymmetric synthesis of (2S,3R)- and (2S,3S)-[2-13C;3-2H] glutamic acids has been successfully achieved with high enantioselectivity, and modifications to this procedure for synthesizing other labeled amino acids are underway.

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