(S)-2-Aminooctanedioic acid

Base Information

• Chemical Name: (S)-2-Aminooctanedioic acid
• CAS No.: 4254-88-0
• Molecular Formula: C8H15 N O4
• Molecular Weight: 189.211
• Hs Code.: 2922499990
• European Community (EC) Number: 224-231-3
• UNII: B347Q73CGH
• DSSTox Substance ID: DTXSID90195333
• Nikkaji Number: J205.668B
• Wikidata: Q27274298
• Mol file: 4254-88-0.mol

Synonyms:(S)-2-Aminooctanedioic acid;4254-88-0;H-ASU-OH;L-alpha-Aminosuberic acid;L-2-Aminosuberic acid;(2S)-2-Aminooctanedioic acid;aminosuberic acid;L-2-aminooctanedioic acid;UNII-B347Q73CGH;B347Q73CGH;EINECS 224-231-3;Octanedioic acid, 2-amino-, (2S)-;L-2-amino suberic acid;(S)-2-Aminooctanedioicacid;alpha-Aminosuberic acid, L-;SCHEMBL4881787;L-ALFA-AMINOSUBERIC ACID;AMINOSUBERIC ACID [INCI];DTXSID90195333;YOFPFYYTUIARDI-LURJTMIESA-N;L-.ALPHA.-AMINOSUBERIC ACID;MFCD00037224;AKOS016842473;L-Asu-OH: L-2-Aminooctanedioic acid;.ALPHA.-AMINOSUBERIC ACID, L-;OCTANEDIOIC ACID, 2-AMINO-, L-;BS-28028;OCTANEDIOIC ACID, 2-AMINO-, (S)-;CS-0199424;L--Aminosuberic acid;A848373;Q27274298

Chemical Property of (S)-2-Aminooctanedioic acid

Chemical Property:

• Vapor Pressure: 5.16E-07mmHg at 25°C
• Boiling Point: 385.5°Cat760mmHg
• Flash Point: 187°C
• PSA: 100.62000
• Density: 1.229g/cm³
• LogP: 1.13370
• Storage Temp.: Store at RT.
• XLogP3: -2.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 189.10010796
• Heavy Atom Count: 13
• Complexity: 181

Purity/Quality:

98% ^*data from raw suppliers

L-α-Aminosuberic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C(CCC(C(=O)O)N)CCC(=O)O
• Isomeric SMILES: C(CC[C@@H](C(=O)O)N)CCC(=O)O

Technology Process of (S)-2-Aminooctanedioic acid

There total 20 articles about (S)-2-Aminooctanedioic 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:

N-(benzyloxycarbonyl)-L-α-aminosuberic acid

N-Chloracetyl-D,L-α-aminosuberinsaeure

(2RS)-α-Ethyl ω-methyl 2-(N-acetylamino)suberate

cyclo[2-aminoisobutyryl-(S)-phenylalanyl-(R)-prolyl-(S)-2-aminosuberoyl-]

Downstream raw materials:

Fmoc-L-Asu-OH

(2S)-N-tert-butoxycarbonyl-2-aminosuberic 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、 Masuoka,Shin-ya,Furihata,Matsumoto,Takebayashi,Nagai,Suzuki,Hayakawa,Seto. "Diheteropeptin, a novel substance with TGF-β-like activity, produced by a fungus, Diheterospora chlamydosporia. II. Physico-chemical properties and structure elucidation". . p. 793 - 798. Retrieved 2007/10/03.