198625-06-8

Basic information

• Product Name: 3(S)-hydroxy-2(R)-monomethoxytrityloxymethyl-N-[(thymin-1-yl)-acetyl] pyrrolidine
• Synonyms: 3(S)-hydroxy-2(R)-monomethoxytrityloxymethyl-N-[(thymin-1-yl)-acetyl] pyrrolidine
• CAS NO: 198625-06-8
• Molecular Weight: 555.631
• Mol File: 198625-06-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3(S)-hydroxy-2(R)-monomethoxytrityloxymethyl-N-[(thymin-1-yl)-acetyl] pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: 3(S)-hydroxy-2(R)-monomethoxytrityloxymethyl-N-[(thymin-1-yl)-acetyl] pyrrolidine(198625-06-8)
• EPA Substance Registry System: 3(S)-hydroxy-2(R)-monomethoxytrityloxymethyl-N-[(thymin-1-yl)-acetyl] pyrrolidine(198625-06-8)

Safety Data

• Hazardous Substances Data: 198625-06-8(Hazardous Substances Data)

Upstream product

• 105017-31-0 (2R,3S)-2-(hydroxymethyl)-3-hydroxypyrrolidine 
• 20924-05-4 thymidyl acetic acid 
• 198625-01-3 3(S)-hydroxy-2(R)-hydroxymethyl-N-[(thymin-1-yl)-acetyl]-pyrrolidine 
• 14470-28-1 mono-4-methoxytrityl chloride 

Relevant articles and documents

Oligonucleotides with 3-hydroxy-N-acetylprolinol as sugar substitute

Fully modified oligonucleotides were synthesised from the 3-O-phosphoramidites of monomethoxytritylated trans-3-hydroxy-N-[(N6-benzoyladenin-9-yl)-acetyl]-prolinol [(2S,3R) and (2R,3S) series], trans-3-hydroxy-N-[(thymin-1-yl)-acetyl]-prolinol [(2S,3R) and (2R,3S) series], and cis-3-hydroxy-N-[(N6-benzoyl-adenin-9-yl)-acetyl]-L-prolinol (2R,3R). Remarkably, as well the L-trans (2R,3S) as the D-trans (2S,3R) all-adenine oligonucleotides are capable of hybridisation with complementary DNA and RNA. With modified all-thymine trans-oligomers no complexation with natural nucleic acids was observed. However, complex formation between two modified strands of the same sense of chirality does occur with formation of a triple stranded complex. The all-thymine oligonucleotides with trans-3-HO-N-acetylprolinol backbone are capable of hybridisation with trans-4-HO-N-acetylprolinol oligoadenylates of the same enantiomeric form in both the D and the L series, and inversely, the all-adenine oligonucleotide with the trans-3-HO conformation hybridises with the trans-4-HO oligothymidylates. While the former interactions have a triple stranded origin, the latter are 1:1 interactions. No interactions were noticed upon mixing oligonucleotide analogues of different sense of chirality. Modified mixed trans-3-HO A,T sequences display no hybridisation with complementary nucleic acids, nor homocomplex formation. The L-cis all-adenine oligonucleotide hybridises with its RNA complement. Several complexes were investigated by circular dichroism and microcalorimetry. In conclusion, the 3-hydroxy-N-acetylprolinol system represents an example of homochiral oligonucleotides built up from two enantiomeric forms and hybridizing both with natural nucleic acids.