L-Proline, 4-amino-, cis- (9CI)

Base Information

• Chemical Name: L-Proline, 4-amino-, cis- (9CI)
• CAS No.: 16257-83-3
• Molecular Formula: C₅H₁₀N₂O₂
• Molecular Weight: 130.147
• Hs Code.: 2933990090
• Mol file: 16257-83-3.mol

Synonyms:L-Proline,4-amino-, cis-; Proline, 4-amino-, L-cis- (8CI)

Chemical Property of L-Proline, 4-amino-, cis- (9CI)

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Boiling Point: 289℃
• PKA: 2.01±0.20(Predicted)
• Flash Point: 128℃
• PSA: 75.35000
• Density: 1.244
• LogP: -0.21070
• Storage Temp.: 2-8°C(protect from light)

Purity/Quality:

99% ^*data from raw suppliers

4-Amino-cis-L-proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: L-Proline, 4-amino-, cis- (9CI), also known as cis-4-amino-L-proline (cAmp), serves as a constrained scaffold in peptide design, particularly for modulating opioid receptor interactions. Its incorporation into endomorphin-2 analogues enhances structural rigidity, improving μ-opioid receptor affinity and activity, with some derivatives achieving nanomolar binding potency. This modification highlights its utility in refining peptide therapeutics for enhanced pharmacological profiles.

Technology Process of L-Proline, 4-amino-, cis- (9CI)

There total 1 articles about L-Proline, 4-amino-, cis- (9CI) 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: 73.0%

(2S,4S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-(tert-butoxycarbonylamino)pyrrolidine2-carboxylic acid (221352-74-5,1253790-74-7) → cis-4-Amino-prolin (16257-83-3,1217598-26-9,21618-64-4,263407-17-6)

Guidance literature:

(2S,4S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-(tert-butoxycarbonylamino)pyrrolidine2-carboxylic acid; With diethylamine; In acetonitrile; at 20 ℃; for 1h; Inert atmosphere;

With trifluoroacetic acid; In dichloromethane; acetonitrile;

upstream raw materials:

(2S,4S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-(tert-butoxycarbonylamino)pyrrolidine2-carboxylic acid

Refernces

Cis-4-amino-l-proline residue as a scaffold for the synthesis of cyclic and linear endomorphin-2 analogues: Part 2

10.1021/jm300947s

The study focuses on the synthesis and evaluation of cyclic and linear analogues of endomorphin-2 (EM-2), a potent opioid peptide. The researchers replaced the native Pro2 residue with cis-4-amino-L-proline (cAmp) to create a more constrained cyclic structure and introduced variations in the stereochemistry of the Phe3 and Phe4 residues to modulate receptor affinity. They synthesized eight new analogues with different stereochemical configurations at the chiral centers of these aromatic residues. The aim was to enhance the affinity and activity towards μ-opioid receptors. The study found that the stereochemical changes led to significant improvements in affinity and activity compared to the prototype compound, with some analogues showing nanomolar binding affinity. The results provide insights into the structural requirements for optimal receptor interaction and could inform the development of more effective opioid therapeutics.