Dl-Alpha-Aminosuberic Acid

Base Information

• Chemical Name: Dl-Alpha-Aminosuberic Acid
• CAS No.: 19641-59-9
• Molecular Formula: C8H15NO4
• Molecular Weight: 189.21
• Mol file: 19641-59-9.mol

Synonyms:DL-2-AMINOOCTANEDIOIC ACID;DL-2-AMINOSUBERIC ACID;H-DL-ASU-OH;(RS)-2-AMINOOCTANEDIOIC ACID;Aminosubericacid;DL-α-Aminosuberic acid;DL-2-aminosubericacid95+%;DL-2-Aminoctanedioic acid

Chemical Property of Dl-Alpha-Aminosuberic Acid

Chemical Property:

• Melting Point: 240 °C
• Boiling Point: 385.5 °C at 760 mmHg
• Flash Point: 187 °C
• PSA: 100.62000
• Density: 1.229g/cm³
• LogP: 1.13370

Purity/Quality:

98%min ^*data from raw suppliers

DL-2-Aminosuberic Acid 97 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Dl-Alpha-Aminosuberic Acid

There total 48 articles about Dl-Alpha-Aminosuberic 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: 43.0%

(2SR)-acetylaminosuberic acid (127027-20-7) → (2R)-acetylaminosuberic acid (918663-85-1) + (2S)-L-α-Aminosuberic acid (4254-88-0,19641-59-9)

Guidance literature:

With sodium hydroxide; acylase I from Aspergillus melleus; cobalt(II) chloride; In phosphate buffer; at 39 ℃; pH=7.2;

DOI:10.1021/jm050214x

Reference yield:

methyl 6-oxohexanoate (6654-36-0) → (2S)-L-α-Aminosuberic acid (4254-88-0,19641-59-9)

Guidance literature:

Multi-step reaction with 3 steps

1: t-BuOK / CH₂Cl₂ / 2 h / -78 °C

2: 99 percent / H₂ / 10percent Pd/C / acetone / 24 h / 3040 Torr / Ambient temperature

3: 6 N HCl / bis-(2-methoxy-ethyl) ether / 48 h / Heating

With hydrogenchloride; potassium tert-butylate; hydrogen; palladium on activated charcoal; In dichloromethane; diethylene glycol dimethyl ether; acetone;

DOI:10.1021/jo00092a029

Reference yield:

2-amino-octanedioic acid (3054-07-7,19641-59-9) → (2S)-L-α-Aminosuberic acid (4254-88-0,19641-59-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / NaHCO₃ / H₂O / 0.17 h / pH 8

2: 43 percent / aq. NaOH; CoCl₂*6H₂O; acylase I from Aspergillus melleus / aq. phosphate buffer / 39 °C / pH 7.2

With sodium hydroxide; acylase I from Aspergillus melleus; sodium hydrogencarbonate; cobalt(II) chloride; In phosphate buffer; water;

DOI:10.1021/jm050214x

upstream raw materials:

2-chloro-octanedioic acid

6-chlorohexanenitrile

2-acetylaminomalonic acid diethyl ester

6-bromo-hexanoic acid ethyl ester

Downstream raw materials:

(2R)-D-α-Aminosuberic acid

Fmoc-L-Asu-OH

2-(((9H-fluoren-9-yl)methoxy)carbonylamino)octanedioic acid

2-(tert-butoxycarbonylamino)octanedioic acid

Refernces

• 1、 Von Bargen, Katharina Walburga,Niehaus, Eva-Maria,Bergander, Klaus,Brun, Reto,Tudzynski, Bettina,Humpf, Hans-Ulrich. "Structure elucidation and antimalarial activity of apicidin F: An apicidin-like compound produced by Fusarium fujikuroi". . p. 2136 - 2140. Retrieved 2014/01/06.
• 2、 Wheatley, Nicole C.,Andrews, Katherine T.,Tran, Truc L.,Lucke, Andrew J.,Reid, Robert C.,Fairlie, David P.. "Antimalarial histone deacetylase inhibitors containing cinnamate or NSAID components". supporting information; experimental part. p. 7080 - 7084. Retrieved 2010/12/25.