847994-36-9

Basic information

• Product Name: 1-Pyrrolidinecarboxylic acid, 2-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-4-hydroxy-, phenylmethyl ester, (2S,4R)-
• CAS NO: 847994-36-9
• Molecular Formula: C18H26N2O5
• Molecular Weight: 350.415
• Mol File: 847994-36-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-Pyrrolidinecarboxylic acid, 2-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-4-hydroxy-, phenylmethyl ester, (2S,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Pyrrolidinecarboxylic acid, 2-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-4-hydroxy-, phenylmethyl ester, (2S,4R)-(847994-36-9)
• EPA Substance Registry System: 1-Pyrrolidinecarboxylic acid, 2-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-4-hydroxy-, phenylmethyl ester, (2S,4R)-(847994-36-9)

Safety Data

• Hazardous Substances Data: 847994-36-9(Hazardous Substances Data)

Upstream product

• 95687-41-5 (2S,4R)-N1-(benzyloxycarbonyl)-4-hydroxy-2-(hydroxymethyl)-pyrrolidine 
• 501-53-1 benzyl chloroformate 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 51-35-4 4R-4-hydroxyproline 
• 64187-48-0 methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 847994-48-3 (2S,4R)-N₁-(benzyloxycarbonyl)-4-hydroxy-2-(aminomethyl)-pyrrolidine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 792916-37-1 (2S,4R)-N₁-(benzyloxycarbonyl)-4-hydroxy-2-(p-toluenesulfonyloxymethyl)-pyrrolidine 
• 847994-45-0 (2S,4R)-N₁-(benzyloxycarbonyl)-4-hydroxy-2-(azidomethyl)-pyrrolidine 

Downstream Products

• 847994-39-2 ethyl 3-[(2S,4S)-2-(tert-butoxycarbonylaminomethyl)-4-(N³-benzoyl-thymin-1-yl)-pyrrolidin-1-yl]-propanoate 
• 500733-24-4 (2S,4R)-2-(tert-butyloxycarbonylaminomethyl)-4-hydroxypyrrolidine 

Relevant articles and documents

Backbone extended pyrrolidine PNA (bepPNA): A chiral PNA for selective RNA recognition

Synthesis of cationic, chiral PNA analogues with an extra atom in the backbone (bepPNA) is reported. The (2S,4S) geometry of the pyrrolidine ring, and an additional carbon atom in the backbone of homopyrimidine-bepPNAs resulted in the optimization of the inter-nucleobase distance, such that selective binding to complementary RNA over DNA was observed in the triplex mode. It was evident from circular dichroism studies that oligomers with mixed aminoethylglycyl-bep (aeg-bep) repeating units, and also bepPNA with homogeneous backbone attained structures quite different from those of aegPNA2:RNA/DNA complexes. The bepPNA, when incorporated in a duplex forming mixed purine-pyrimidine sequence, also showed a preference for binding complementary RNA over DNA.

Synthesis of trans-L/D-2-(tert-butoxycarbonylaminomethyl)-4-(thymin-1-yl) pyrrolidin-1-yl acetic acid

To delineate the binding preferences of stereochemically divergent pyrrolidine PNAs, synthesis of all four diastreomeric monomers of I and the systematic complexation studies of the resultant PNAs with complementary DNA/ RNA is essential. We herein report the synthesis of trans-L/D-2-(tert-butoxycarbonylaminomethyl)-4-(thymin-1-yl) pyrrolidin-1-yl acetic acids I, their incorporation in PNA oligomers and DNA binding studies will be presented.