D-GlutaMic Acid-13C5

Base Information

• Chemical Name: D-GlutaMic Acid-13C5
• CAS No.: 1202063-54-4
• Molecular Formula: C₅H₉NO₄
• Molecular Weight: 155.053
• Mol file: 1202063-54-4.mol

Synonyms:

Chemical Property of D-GlutaMic Acid-13C5

Chemical Property:

• Storage Temp.: Refrigerator

Purity/Quality:

D-Glutamic Acid-13C5 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Isotope labelled D-Glutamic Acid (G596965) is the unnatural (R)-enantiomer of Glutamic Acid, a non-essential amino acid. Its salt form (glutamate) is an important neurotransmitter that plays a key role in long-term potentiation and is important for learning and memory. Glutamic Acid is also a key molecule in cellular metabolism.

Technology Process of D-GlutaMic Acid-13C5

There total 4 articles about D-GlutaMic Acid-13C5 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: 74.0%

C5(13)C5H13(2)H2(15)NO5 (1259016-71-1) → (2S,3S,4R)-[3,4-(2)H2;1,2,3,4,5-(13)C5;2-(15)N]glutamic acid (554428-56-7,108395-12-6,1202063-54-4,206983-94-0,95388-01-5)

Guidance literature:

C₅⁽¹³⁾C₅H₁₃⁽²⁾H₂⁽¹⁵⁾NO₅; With hydrogenchloride; In water; at 110 ℃; for 3h;

With water; sodium hydroxide; In dichloromethane; for 24h; pH=3; Cooling;

DOI:10.1021/ol1026766

Reference yield:

(2S)-[2,3,4,5,6-(13)C5;1-(15)N]N-tert-butoxycarbonyl-5-(tert-butyldimethylsilyloxymethyl)-1H-pyrrol-2(5H)-one (1259016-65-3) → (2S,3S,4R)-[3,4-(2)H2;1,2,3,4,5-(13)C5;2-(15)N]glutamic acid (554428-56-7,108395-12-6,1202063-54-4,206983-94-0,95388-01-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: palladium 10% on activated carbon; deuterium / ethyl [2]alcohol / 2 h

2.1: acetic acid / 21 h / 20 °C

3.1: sodium periodate; ruthenium trichloride / water; acetone / 5 - 20 °C

4.1: hydrogenchloride / water / 3 h / 110 °C

4.2: 24 h / pH 3 / Cooling

With hydrogenchloride; ruthenium trichloride; sodium periodate; palladium 10% on activated carbon; acetic acid; deuterium; In ethyl [2]alcohol; water; acetone;

DOI:10.1021/ol1026766

Reference yield:

(2S,3S,4R)-[3,4-(2)H2;2,3,4,5,6-(13)C5;1-(15)N]N-tert-butoxycarbonyl-5-(tert-butyldimethylsilyloxymethyl)pyrrolidin-2-one (554428-67-0) → (2S,3S,4R)-[3,4-(2)H2;1,2,3,4,5-(13)C5;2-(15)N]glutamic acid (554428-56-7,108395-12-6,1202063-54-4,206983-94-0,95388-01-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: acetic acid / 21 h / 20 °C

2.1: sodium periodate; ruthenium trichloride / water; acetone / 5 - 20 °C

3.1: hydrogenchloride / water / 3 h / 110 °C

3.2: 24 h / pH 3 / Cooling

With hydrogenchloride; ruthenium trichloride; sodium periodate; acetic acid; In water; acetone;

DOI:10.1021/ol1026766

upstream raw materials:

¹³C₅-¹⁵N₂-L-glutamine

(2S)-[2,3,4,5,6-⁽¹³⁾C₅;1-⁽¹⁵⁾N]N-tert-butoxycarbonyl-5-(tert-butyldimethylsilyloxymethyl)-1H-pyrrol-2(5H)-one

(2S,3S,4R)-[3,4-⁽²⁾H₂;2,3,4,5,6-⁽¹³⁾C₅;1-⁽¹⁵⁾N]N-tert-butoxycarbonyl-5-(tert-butyldimethylsilyloxymethyl)pyrrolidin-2-one

C₅⁽¹³⁾C₅H₁₃⁽²⁾H₂⁽¹⁵⁾NO₅

Downstream raw materials:

(2S,3S,4R)-[1,2,3,4,5-13C5;2,5-13N2;3,4-2H2]glutamine

SAIL proline

C₉⁽¹³⁾C₅H₁₆N₂O₆

C₇⁽¹³⁾C₅H₁₄N₂O₅

Refernces

• 1、 Terauchi, Tsutomu,Kamikawai, Tomoe,Vinogradov, Maxim G.,Starodubtseva, Eugenia V.,Takeda, Mitsuhiro,Kainosho, Masatsune. "Synthesis of stereoarray isotope labeled (SAIL) lysine via the "head-to-tail" conversion of SAIL glutamic acid". . p. 161 - 163. Retrieved 2011/03/20.