15871-58-6

Basic information

• Product Name: rac trans-3-Amino-1-oxyl-2,2,5,5-tetramethylpyrrolidine-4-carboxylic Acid
• Synonyms: rac trans-3-Amino-1-oxyl-2,2,5,5-tetramethylpyrrolidine-4-carboxylic Acid;(3R,4R)-rel-3-AMino-4-carboxy-2,2,5,5-tetraMethyl-1-pyrrolidinyloxy
• CAS NO: 15871-58-6
• Molecular Formula: C9H18N2O3
• Molecular Weight: 202.25082
• Product Categories: Heterocycles;Spin Labeling Compounds;Heterocycles, Spin Labeling Compounds
• Mol File: 15871-58-6.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: rac trans-3-Amino-1-oxyl-2,2,5,5-tetramethylpyrrolidine-4-carboxylic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: rac trans-3-Amino-1-oxyl-2,2,5,5-tetramethylpyrrolidine-4-carboxylic Acid(15871-58-6)
• EPA Substance Registry System: rac trans-3-Amino-1-oxyl-2,2,5,5-tetramethylpyrrolidine-4-carboxylic Acid(15871-58-6)

Safety Data

• Hazardous Substances Data: 15871-58-6(Hazardous Substances Data)

Usage

Uses

A spin-label.

InChI:InChI=1/C9H17N2O3/c1-8(2)5(7(12)13)6(10)9(3,4)11(8)14/h5-6H,10H2,1-4H3,(H,12,13)/t5-,6+/m0/s1

Relevant articles and documents

Synthesis, resolution and assignment of absolute configuration of trans 3-amino-1-oxyl-2,2,5,5-tetramethylpyrrolidine-4-carboxylic acid (POAC), a cyclic, spin-labelled β-amino acid

Racemic trans 3-(9-fluorenylmethyloxycarbonylamino)-1-oxyl-2,2,5,5-tetramethylpyrrolid ine-4-carboxylic acid (Fmoc-POAC-OH), prepared by conventional methods, was resolved upon esterification with (aR)-2,2′-dihydroxy-1,1′-binaphthyl. Separation of the obtained diastereomeric monoesters Fmoc-(±)-trans-POAC-O-(aR)-binaphthol by crystallization/chromatography, and removal of the chiral auxiliary by saponification of the aryl ester function furnished both enantiomers (+)-(3R,4R)-Fmoc-POAC-OH and (-)-(3S,4S)-Fmoc-POAC-OH. The absolute configuration of the asymmetric C3, C4 carbons of POAC were assigned from the induced circular dichroism of a flexible biphenyl probe present in the terminally protected dipeptide derivatives Boc-Bip-(+)-POAC-OMe and Boc-Bip-(-)-POAC-OMe (Bip, 2′,1′:1,2;1″,2″:3,4-dibenzcyclohepta-1,3-diene-6 -amino-6-carboxylic acid). This assignment was confirmed by X-ray diffraction analysis of the diastereomeric monoester Fmoc-(+)-trans-POAC-O-(aR)-binaphthol, shown to be (aR,3R,4R). Solution synthesis of peptides to the hexamer level, based on the (3R,4R)-POAC enantiomer combined with (1S,2S)-2-aminocyclopentane-1-carboxylic acid, was carried out to examine coupling conditions at both C- and N-termini of the POAC residue, in view of further syntheses and 3D-structural investigations.