419564-82-2

Upstream product

• 100-46-9 benzylamine 
• 201536-29-0 1,3(R):4,6(R)-bis-O-(4-methoxybenzylidene)-D-mannitol 

Downstream Products

• 419564-76-4 (2R,3R,4R,5R)-3,4-Bis-benzyloxy-2,5-bis-{[((S)-3-methyl-1-methylcarbamoyl-butylcarbamoyl)-methyl]-carbamoyl}-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 419564-79-7 (2R,3R,4R,5R)-3,4-Bis-benzyloxy-2,5-bis-{[((S)-1-methoxycarbonyl-3-methyl-butylcarbamoyl)-methyl]-carbamoyl}-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 419564-87-7 (2S,3R,4R,5S)-3,4-Bis-benzyloxy-2,5-bis-(4-methoxy-benzyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 419564-84-4 (2S,3R,4R,5S)-3,4-Dihydroxy-2,5-bis-(4-methoxy-benzyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 419564-85-5 (2S,3R,4R,5S)-3,4-Bis-benzyloxy-2,5-bis-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 419564-83-3 (2S,3R,4R,5S)-1-Benzyl-2,5-bis-(4-methoxy-benzyloxymethyl)-pyrrolidine-3,4-diol 

Relevant academic research and scientific papers

Studies on novel peptidomimetics having bi-directional dispositions of hydroxylated D-Pro-Gly motifs anchored on a C2-symmetric iminosugar-based foundation

A rigid pyrrolidine based scaffold comprising of 2,5-dideoxy-2,5-imino-D-idaric acid (1) is developed. Attachment of peptide strands to the carboxylic groups at both ends of this novel template led to the peptidomimetics 2 and 3. Conformational analysis by NMR studies revealed that compounds 2b, 3b and 2c, 3c take interesting turn structures (C2 symmetric for 2c and 3c) in DMSO-d6 consisting of identical intramolecular hydrogen bonds at two ends between LeuNH → sugar-OH as depicted in structure A, whereas 2a and 3a display structures with regular β-turns with hydrogen bonds between LeuNH → Boc-C=0 in one-half of their molecular frameworks (structure B), characteristic of the turn structures commonly observed in "D-Pro-Gly"-containing peptides. These results suggest that a cis hydroxyl group at the 3-position of the proline residue favors a pseudo β-turn-like nine-membered ring structure in hydroxyproline-containing peptides involving an intramolecular hydrogen bond between the hydroxyl and the i + 2 backbone amide.