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:

97% ^*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:

• General Description: DL-α-Aminosuberic acid (also known as DL-2-aminooctanedioic acid or DL-2-aminosuberic acid) is a dicarboxylic amino acid derivative used as an intermediate in peptide synthesis, particularly for creating dicarba analogues of cystine peptides. These analogues exhibit enhanced stability and biological activity due to the replacement of reducible disulfide bonds with non-reducible dicarba bridges. Dl-Alpha-Aminosuberic Acid can be synthesized through methods like Kolbe electrolytic dimerization of protected glutamic acid derivatives, allowing for the retention of stereochemistry and selective protection of functional groups. Its utility lies in enabling the preparation of structurally modified peptides with improved properties.

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:

6-(5-methyl-2-oxo-2,3-dihydro-1H-imidazol-4-yl)-hexanoic acid

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

(2R)-D-α-Aminosuberic acid

2-(tert-butoxycarbonylamino)octanedioic acid

Refernces

Useful Intermediates for Synthesis of Dicarba Analogues of Cystine Peptides: Selectively Protected α-Aminosuberic Acid and α,α'-Diaminosuberic Acid of Defined Stereochemistry

10.1021/jo01303a028

The research describes practical procedures for synthesizing selectively protected a-aminosuberic acid and a,a'-diaminosuberic acid using mixed Kolbe electrolytic decarboxylative dimerization of different carboxylic acids. The purpose of the study is to develop a method for creating these intermediates, which are useful in the preparation of dicarba and desaminodicarba analogues of cystine peptides, known for their high biological activity and enhanced stability due to the absence of reducible disulfide linkages. The key chemicals used include a-tert-butyl N-Boc-L-glutamate (2a), a-methyl N-Cbz-L-glutamate (1), a-tert-butyl N-Boc-D-glutamate (2b), and methyl glutarate (8). The study concludes that by using readily available selectively blocked glutamic acid derivatives and incorporating desired protecting groups and stereochemistry prior to Kolbe dimerization, the desired unsymmetrical dimers can be isolated without racemization of chiral centers. The method provides a practical and efficient way to synthesize optically pure, selectively protected diamino- and monoamino suberic acid derivatives for use in peptide synthesis.

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 19641-59-9 Dl-Alpha-Aminosuberic Acid

Send

Send

Metric Ton KG G Pound L ML

Send

Send