5-CYANO-DL-TRYPTOPHAN

Base Information

• Chemical Name: 5-CYANO-DL-TRYPTOPHAN
• CAS No.: 139393-02-5
• Molecular Formula: C12H11N3O2
• Molecular Weight: 229.238
• Hs Code.: 2933990090
• Mol file: 139393-02-5.mol

Synonyms:DL-2-AMINO-3-(5-CYANOINDOLYL)PROPIONIC ACID;H-5-CYANO-DL-TRP-OH;5-CYANO-DL-TRYPTOPHAN;RARECHEM AH BS 0097

Chemical Property of 5-CYANO-DL-TRYPTOPHAN

Chemical Property:

• PSA: 102.90000
• LogP: 1.69428
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C

Purity/Quality:

99% ^*data from raw suppliers

(S)-2-Amino-3-(5-cyano-1H-indol-3-yl)propanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (S)-2-Amino-3-(5-cyano-1H-indol-3-yl)propanoic Acid is used in the preparation of tryptophan analogues.

Technology Process of 5-CYANO-DL-TRYPTOPHAN

There total 7 articles about 5-CYANO-DL-TRYPTOPHAN 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: 79.0%

1H-indole-5-carbonitrile (15861-24-2,142396-06-3) + L-serin (56-45-1,83245-15-2) → (S)-5-cyanotryptophan (139393-02-5)

Guidance literature:

With Tm₂F₃ enzyme; In aq. phosphate buffer; water; dimethyl sulfoxide; at 75 ℃; for 12h; pH=8; Enzymatic reaction;

DOI:10.1021/jacs.7b05007

Reference yield:

5-cyano-DL-tryptophan → C12H11N3O2 + (S)-5-cyanotryptophan (139393-02-5)

Guidance literature:

With IvoA acetyltransferase; ATP; magnesium chloride; In aq. phosphate buffer; at 20 ℃; for 12h; pH=7.5; enantioselective reaction;

DOI:10.1021/jacs.9b08898

Reference yield:

5-Cyano-L-tryptophan methyl ester (139393-04-7) → (S)-5-cyanotryptophan (139393-02-5)

Guidance literature:

With sodium carbonate; at 65 ℃;

DOI:10.1016/S0040-4039(00)77665-9

upstream raw materials:

copper(I) cyanide

(2S,3aR,8aR)-8-Acetyl-5-bromo-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid dimethyl ester

5-Cyano-L-tryptophan methyl ester

L-(2β,3aα,8aα)-8-acetyl-1,2-dimethoxycarbonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole

Refernces

• 1、 Dua, Rajesh K.,Phillips, Robert S.. "Synthesis of 5-cyano-I-tryptophan". . p. 29 - 32. Retrieved 1992.
• 2、 Hai, Yang,Jenner, Matthew,Tang, Yi. "Complete Stereoinversion of l -Tryptophan by a Fungal Single-Module Nonribosomal Peptide Synthetase". supporting information. p. 16222 - 16226. Retrieved 2019/10/14.