196937-78-7

Basic information

• Product Name: 2-Benzoylamino-thiazole-5-carboxylic acid {(1R,2S,3R,4R)-4-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-2-methoxy-cyclopentyl}-amide
• CAS NO: 196937-78-7
• Molecular Weight: 693.821
• Mol File: 196937-78-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-Benzoylamino-thiazole-5-carboxylic acid {(1R,2S,3R,4R)-4-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-2-methoxy-cyclopentyl}-amide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Benzoylamino-thiazole-5-carboxylic acid {(1R,2S,3R,4R)-4-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-2-methoxy-cyclopentyl}-amide(196937-78-7)
• EPA Substance Registry System: 2-Benzoylamino-thiazole-5-carboxylic acid {(1R,2S,3R,4R)-4-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-2-methoxy-cyclopentyl}-amide(196937-78-7)

Safety Data

• Hazardous Substances Data: 196937-78-7(Hazardous Substances Data)

Upstream product

• 196937-73-2 2-Benzoylamino-thiazole-5-carboxylic acid ((2R,3S,3aR,9aR)-5,5,7,7-tetraisopropyl-3-methoxy-hexahydro-4,6,8-trioxa-5,7-disila-cyclopentacycloocten-2-yl)-amide 
• 196937-64-1 ((2R,3S,3aR,9aR)-5,5,7,7-Tetraisopropyl-3-methoxy-hexahydro-4,6,8-trioxa-5,7-disila-cyclopentacycloocten-2-yl)-carbamic acid tert-butyl ester 
• 153011-44-0 (1R,2R,3R,4R)-1-tert-butoxycarbonylamino-2-hydroxy-3,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-hydroxymethylcyclopentane 
• 79200-55-8 (1R,4S,5R,6S)-5,6-dihydroxy-2-azabicyclo[2.2.1]heptan-3-one 
• 98-88-4 benzoyl chloride 
• 85026-59-1 (-)-(1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-(hydroxymethyl)cyclopentane 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 196937-82-3 2-Benzoylamino-thiazole-5-carboxylic acid ((1R,2S,3R,4R)-3-hydroxy-4-hydroxymethyl-2-methoxy-cyclopentyl)-amide 
• 196937-70-9 2-Benzoylamino-thiazole-5-carboxylic acid ethyl ester 
• 196937-65-2 (2R,3S,3aR,9aR)-5,5,7,7-Tetraisopropyl-3-methoxy-hexahydro-4,6,8-trioxa-5,7-disila-cyclopentacycloocten-2-ylamine 
• 196937-71-0 2-Benzoylamino-thiazole-5-carboxylic acid 
• 153064-90-5 (-)-(1R, 2S, 3R, 4R)-tert-butyl N-[2,3-dihydroxy-4-(hydroxymethyl)-1-cyclopentyl] carbamate 
• 771428-01-4 (1S,2R,3S,4R)-4-Amino-2,3-dihydroxy-cyclopentanecarboxylic acid methyl ester 
• 445469-11-4 (1S,2R,3S,4R)-4-amino-2,3-dihydroxycyclopentanecarboxylic acid 

Relevant articles and documents

136. Triple-Helix Formation by Pyrimidine Oligonucleotides Containing Nonnatural Nucleosides with Extended Aromatic Nucleobases: Intercalation from the Major Groove as a Method for Recognizing C·G and T·a Base Pairs

The sequence-specific recognition of double-helical DNA by oligonucleotide-directed triple helix formation is limited primarily to purine tracts. To identify potential lead compounds which are able to extend the sequence repertoire of triple helical complexes, we designed two carbocyclic nucleosides with nucleobases attached via amide bonds. N 5-[(1R,2S,3R,4R)-3-hydroxy-4-(hydroxymethyl)-2-methoxycyclopentyl]-2- {[1H-pyrrol-2-yl)carbonyl]-amino}thiazole-5-carboxamide (L1) and 2-benzamido-N 5-[(1R,2S,3R,4R)-3-hydroxy-4-(hydroxymethyl)-2-methoxycyclopentyl] thiazole-5-carboxamide (L2) were synthesized and incorporated into pyrimidine oligonucleotides. The 2-(trimethylsilyl)ethoxymethyl (SEM) protecting group for the 1H-pyrrole NH was found to be compatible with DNA solid-phase synthesis of pyrimidine oligonucleotides. By quantitative DNase I footprinting analysis, both nonnatural nucleosides L1 and L2 showed preferential binding of pyrimidine over purine bases: L1/2 · (C-G) ≈ L1/2 · (T · A) > L1/2?(G · C) ≈ L1/2 · (A · T). Comparison with the previously reported nonnatural nucleosides with extended aromatic nucleobases 1-(2-deoxy-β-D-ribofuranosyl)-4-(3-benzamidophenyl)-imidazole (D3) and N4-[6-(benzamido)pyridin-2-y1]-2′-deoxycytidine (bzM) suggests that the observed binding selectivity C · G ≈ T · A > G · C ≈A · T for the nucleoside analogs L1, L2, D3, and bzM is derived from sequencespecific intercalation with preferential stacking of their nucleobases over pyrimidine · purine Watson-Crick base pairs.