63358-47-4

Basic information

• Product Name: (+)-ALLO-OCTOPINE
• Synonyms: N2-[(S)-1-CARBOXYETHYL]-L-ARGININE;L-(+)-ALLO-OCTOPINE;(+)-ALLO-OCTOPINE;BOC-PROPARGYL-GLY-OHDCHA;N2-[(1S)-1-Carboxyethyl]-L-arginine
• CAS NO: 63358-47-4
• Molecular Formula: C₉H₁₈N₄O₄
• Molecular Weight: 246.26
• Product Categories: Amino Acids & Derivatives
• Mol File: 63358-47-4.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• Solubility: Methanol (Slightly), Water (Slightly, Sonicated)
• Stability: Hygroscopic
• CAS DataBase Reference: (+)-ALLO-OCTOPINE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-ALLO-OCTOPINE(63358-47-4)
• EPA Substance Registry System: (+)-ALLO-OCTOPINE(63358-47-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 63358-47-4(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

A competitive inhibitor of Octopine (O239850). Inhibits callus proliferation in apple.

Upstream product

• 10009-70-8 R-(+)-2-bromopropionic acid 
• 74-79-3 L-arginine 
• 598-72-1 2-Bromopropionic acid 
• 127-17-3 2-oxo-propionic acid 
• 81397-95-7 (R)-2-bromo-5-acetamidopentanoic acid 
• 14527-26-5 2-methylisothiourea sulphate 

Downstream Products

• 463-00-3 4-guanidinobutyric acid 
• 75-07-0 acetaldehyde 
• 57-13-6 urea 

Relevant articles and documents

Configuration of Alanine Part in Natural Octopine

Octopine has a structure of N2-(1-carboxyethyl)arginine or N-(1-carboxy-4-guanidinobutyl)alanine.Configuration of the arginine part in natural octopine is determined as (S), whereas that of the alanine part has been assumed as (R).The configuration of the alanine part was concluded to be (R) by the present synthesis of (+)-octopine, which was identical with the natural one, by a sequence of reactions starting from (R)-alanine and (R)-2-bromo-5-acetamidopentanoic acid.The reaction of (R)-alanine and (R)-2-bromo-5-acetamidopentanoic acid in alkaline conditions gave N2--N5-acetyl-(S)-ornithine which was converted to N2--(S)-ornithine by hydrolysis with hydrochloric acid. (R),(S)-Octopinic acid gave (+)-octopine by guanidination.The reaction of (S)-alanine and (R)-2-bromo-5-acetamidopentanoic acid led to give (S),(S)-octopinic acid and subsequently (+)-isooctopine .