127682-76-2Relevant academic research and scientific papers
Synthesis and structural characterization of homochiral homo-oligomers of parent cis- and trans-furanoid-β-amino acids
Pandey, Sunil K.,Jogdand, Ganesh F.,Oliveira, Joao C. A.,Mata, Ricardo A.,Rajamohanan, Pattuparambil R.,Ramana, Chepuri V.
, p. 12946 - 12954 (2011)
The synthesis of homochiral homo-oligomers of cis- and trans-3- aminotetrahydrofuran-2-carboxylic acids (parent cis- and trans-furanoid-β- amino acids, referred to as "cis-/trans-FAA") has been carried out to understand their secondary structures and their dependence on the ring heteroatom. The oligomers of two diastereomers have been shown to have a distinct left-handed helicity. The cis-FAA homo-oligomers show a 14-helix structure, in contrast to the homo-oligomers of cis-ACPC, which adopt a sheet like structure. The trans-FAA homo-oligomers were found to adopt a 12-helix structure, the same trend found in trans-ACPC homo-oligomers. With the help of ab initio calculations, the structural features of cis-ACPC and cis-FAA hexamers were compared. We believe that the more compact packing of the cis-FAA hexapeptide should be due to a more favorable interaction between the ring and the backbone amide hydrogen. It's the heteroatom that counts: trans-Furanoid-β-amino acid (FAA) homo-oligomers adopt a 12-helix structure similar to that of trans-ACPC (2-aminocyclopentane carboxylic acid) oligomers. However, cis-FAA oligomers seem to adopt 14-helix solution structures, which is in contrast to cis-ACPC oligomers, for which a sheetlike structure has been observed. Calculations reveal that this preference in cis-FAAs is due to a more favorable contact between the backbone and the ring (see scheme). Copyright
Synthesis of isomeric dideoxynucleosides with partial symmetry
Nair,Zintek,Geun Sook Jeon
, p. 389 - 391 (1995)
Approaches to the synthesis of (S) and (R) enantiomers of hydroxymethylated isodideoxynucleosides have been developed. Because of the symmetry introduced at the carbon that normally bears the -CH2OH group, these compounds have only one asymmetric center and each enantiomeric series may be viewed as being both D- and L-related.
Synthesis of 5-substituted-3-[(2'S,3'S)-3'-hydroxy-2'-hydroxymethyltetrahydrofuran-3'-yl]-1,2,4-oxadiazoles and their epimers
Wu,Ma,Zhang,Lu,Guo,Zheng
, p. 1527 - 1536 (2007/10/03)
5-Phenyl-3-[(2'R,3'S)-3'-hydroxy-2'-dimethoxymethyltetrahydrofuran-3'-yl]-1,2,4-oxadiazole 10a and its epimer 11a, 5-methyl-3-[(2'R,3'S)-3'-hydroxy-2'-dimethoxymethyltetrahydrofuran-3'-yl]-1,2,4-oxadiazole 10b and its epimer 11b were synthesized from cyan
THE SYNTHESIS OF (S) AND (R) ENANTIOMERS OF NOVEL HYDROXYMETHYLATED ISODIDEOXYNUCLEOSIDES
Zintek, Lawrence B.,Jeon, Geun Sook,Nair, Vasu
, p. 1853 - 1864 (2007/10/02)
Novel isomeric dideoxynucleosides, with symmetry introduced at the 2'-position (4'-position using normal nucleoside numbernig) through the introduction of an additional hydroxymethyl group, have been synthesized.Both (R) and (S) enantiomeric series were investigated.The methodologies developed have generality and the presence of the hydroxymethyl group trans to the base may be used to introduce a wide variety of functionalities at this position.
Synthesis and anti-HIV activity of isonucleosides
Huryn,Sluboski,Tam,Weigele,Sim,Anderson,Mitsuya,Broder
, p. 2347 - 2354 (2007/10/02)
A series of isomeric 2',3'-dideoxynucleosides which contains a modified carbohydrate moiety has been prepared. This class of compounds was designed to mimic the activity of known anti-HIV dideoxynucleosides, while imparting enhanced chemical and enzymatic
SYNTHESYS OF ISO-DDA, MEMBER OF A NOVEL CLASS OF ANTI-HIV AGENTS
Huryn, Donna M.,Sluboski, Barbara C.,Tam, Steve Y,,Todaro, Luis J.,Weigele, Manfred
, p. 6259 - 6262 (2007/10/02)
Iso-ddA (3) represents a new class of potential anti-AIDS drugs.Synthetic approaches to this compound involving nucleophilic additions to a novel carbohydrate framework are discussed.
