5-Aminopentanoate

Base Information

• Chemical Name: 5-Aminopentanoate
• CAS No.: 660-88-8
• Molecular Formula: C5H11NO2
• Molecular Weight: 117.148
• Hs Code.: 29224999
• Wikidata: Q106315172
• Mol file: 660-88-8.mol

Synonyms:5-azaniumylpentanoate;5-aminopentanoate;5-ammoniopentanoate;5-aminopentanoic acid zwitterion;5-aminovalerate;delta-aminovalerate;delta-Amino-n-valerate;delta-amino-valeric acid;CHEBI:356010;BDBM50137035

Chemical Property of 5-Aminopentanoate

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Melting Point: 158-161 °C(lit.)
• Refractive Index: 1.4650 (estimate)
• Boiling Point: 247.5 °C at 760 mmHg
• PKA: 4.27(at 25℃)
• Flash Point: 103.5 °C
• PSA: 63.32000
• Density: 1.071 g/cm³
• LogP: 0.90030
• Storage Temp.: Store at 0-5°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly), Water (Slightly)
• XLogP3: -2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 117.078978594
• Heavy Atom Count: 8
• Complexity: 67.3

Purity/Quality:

98%, ^*data from raw suppliers

5-Aminovaleric acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CC[NH3+])CC(=O)[O-]
• General Description: 5-Aminovaleric acid (δAva) was utilized in the synthesis of Gramicidin S analogs, where it replaced L-leucyl-p-phenylalanyl residues to form [3-4-δAva]-GS and [3-4,3'-4'-bis(δAva)]-GS. The study demonstrated that incorporating 5-aminovaleric acid into the GS structure influenced the antimicrobial activity of the resulting analogs, highlighting the importance of amide bonds and side chains in the peptide's biological function. This suggests that 5-aminovaleric acid can serve as a flexible linker or modifier in peptide design, potentially altering the physicochemical and bioactive properties of the parent molecule.

Technology Process of 5-Aminopentanoate

There total 44 articles about 5-Aminopentanoate 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: 95.0%

piperidin-2-one (675-20-7) → 5-aminopentanoic acid (660-88-8)

Guidance literature:

With barium hydroxide octahydrate; water; for 48h; Reflux;

DOI:10.24820/ark.5550190.p010.905

Reference yield: 95.0%

L-lysine (56-87-1,3506-25-0) → 5-aminopentanoic acid (660-88-8)

Guidance literature:

With water; at 37 ℃; for 5h; Enzymatic reaction;

DOI:10.1016/j.molcatb.2009.12.006

Reference yield: 71.0%

5-hydroxypentylamine (2508-29-4) → 5-aminopentanoic acid (660-88-8)

Guidance literature:

5-hydroxypentylamine; With (6-di-tert-butylphosphinomethyl-2,2’-bipyridyl)Ru(CO)HCl; water; sodium hydroxide; In 1,4-dioxane; for 24h; Schlenk technique; Inert atmosphere; Glovebox; Reflux;

With hydrogenchloride; In 1,4-dioxane; water;

DOI:10.1021/jacs.6b03488

upstream raw materials:

piperidin-2-one

Adipic acid

N-benzoylpiperidine

2-(3-bromopropyl)isoindole-1,3-dione

Downstream raw materials:

5-(N-phthalimido)pentanoic acid

5-benzoylaminopentanoic acid

δ-aminovaleric acid ethyl ester

5-p-toluoylamino-valeric acid

Refernces

Synthesis of gramicidin S (GS) analogs, [3-4-δAva]-GS and [3-4,3'-4'-bis(δAva)-GS (δAva=5-aminovaleric acid)

10.1246/bcsj.59.185

The research focuses on the synthesis and evaluation of Gramicidin S (GS) analogs, specifically [3Ava5-]-GS and [3Ava4,3'-]-GS, where Ava represents 5-Aminovaleric Acid. These analogs involve replacing one or two L-leucyl-p-phenylalanyl residues of GS with 5-aminovaleric acid residues. Various chemicals played crucial roles in the synthesis process. For instance, Boc-Val-Orn(Z)-OH, H-Leu-D-Phe-Pro-OMe, and Boc-Pro-OH were used as starting materials or intermediates. Reagents like DCC (dicyclohexylcarbodimide), HOBt (1-hydroxybenzotriazole), and isopentyl nitrite were employed in coupling and conversion reactions. Solvents such as THF (tetrahydrofuran), DMF (N,N-dimethylformamide), and MeOH (methanol) were utilized in different steps of the synthesis. The study also involved the use of protecting groups like Boc (t-butoxycarbonyl) and Z (benzyloxycarbonyl), and their removal was achieved using methods involving HCI (hydrochloric acid) and Pd (palladium) catalysts. The synthesized analogs were characterized and their antimicrobial activities were assessed, revealing insights into the contributions of the amide bond and side chains in the GS structure to its antimicrobial properties.