15384-34-6Relevant articles and documents
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Gorin,Perlin
, p. 693,699 (1956)
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New approach to (-)-polyoxamic acid and 3,4-diepipolyoxamic acid from d-lyxono-1,4-lactone
Falentin, Céline,Beaupère, Daniel,Demailly, Gilles,Stasik, Imane
, p. 9989 - 9991 (2008)
The non-natural enantiomer of polyoxamic acid (1) and 3,4-diepipolyoxamic acid (2) was synthesized in four steps from d-lyxono-1,4-lactone (4). Regioselective bromination of unprotected d-lyxono-1,4-lactone with HBr/AcOH led to 2-bromo-2-deoxy-d-xylono-1,
Prebiotic synthesis of 2-deoxy-d-ribose from interstellar building blocks promoted by amino esters or amino nitriles
Steer, Andrew M.,Bia, Nicolas,Smith, David K.,Clarke, Paul A.
supporting information, p. 10362 - 10365 (2017/09/25)
Understanding the prebiotic genesis of 2-deoxy-d-ribose, which forms the backbone of DNA, is of crucial importance to unravelling the origins of life, yet remains open to debate. Here we demonstrate that 20 mol% of proteinogenic amino esters promote the selective formation of 2-deoxy-d-ribose over 2-deoxy-d-threopentose in combined yields of ≥4%. We also demonstrate the first aldol reaction promoted by prebiotically-relevant proteinogenic amino nitriles (20 mol%) for the enantioselective synthesis of d-glyceraldehyde with 6% ee, and its subsequent conversion into 2-deoxy-d-ribose in yields of ≥ 5%. Finally, we explore the combination of these two steps in a one-pot process using 20 mol% of an amino ester or amino nitrile promoter. It is hence demonstrated that three interstellar starting materials, when mixed together with an appropriate promoter, can directly lead to the formation of a mixture of higher carbohydrates, including 2-deoxy-d-ribose.
A heterogeneous Pd-Bi/C catalyst in the synthesis of l-lyxose and l-ribose from naturally occurring d-sugars
Fan, Ao,Jaenicke, Stephan,Chuah, Gaik-Khuan
supporting information; experimental part, p. 7720 - 7726 (2011/12/04)
A critical step in the synthesis of the rare sugars, l-lyxose and l-ribose, from the corresponding d-sugars is the oxidation to the lactone. Instead of conventional oxidizing agents like bromine or pyridinium dichromate, it was found that a heterogeneous catalyst, Pd-Bi/C, could be used for the direct oxidation with molecular oxygen. The composition of the catalyst was optimized and the best results were obtained with 5:1 atomic ratio of Pd:Bi. The overall yields of the five-step procedure to l-ribose and l-lyxose were 47% and 50%, respectively. The synthetic procedure is advantageous from the viewpoint of overall yield, reduced number of steps, and mild reaction conditions. Furthermore, the heterogeneous oxidation catalyst can be easily separated from the reaction mixture and reused with no loss of activity.
