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L-Deoxyribose

Summary

l-Deoxyribose is an organic compound with formula C5H10O4. It is a synthetic monosaccharide, a stereoisomer (mirror image) of the natural compound d-deoxyribose.

l-Deoxyribose
Names
IUPAC name
(3R,4S)-3,4,5-Trihydroxypentanal
Other names
2-Deoxy-l-erythro-pentose; 2-Deoxy-l-ribose; l-2-Deoxyribose
Identifiers
  • 18546-37-7 checkY
3D model (JSmol)
  • Interactive image
  • hemiacetal: Interactive image
ChemSpider
  • 5362530 ☒N
  • 8031184 hemiacetal ☒N
ECHA InfoCard 100.131.283 Edit this at Wikidata
  • 6994527
  • 9855484 hemiacetal
  • DTXSID50939972 Edit this at Wikidata
  • InChI=1S/C5H10O4/c6-2-1-4(8)5(9)3-7/h2,4-5,7-9H,1,3H2/t4-,5+/m1/s1 ☒N
    Key: ASJSAQIRZKANQN-UHNVWZDZSA-N ☒N
  • InChI=1/C5H10O4/c6-2-1-4(8)5(9)3-7/h2,4-5,7-9H,1,3H2/t4-,5+/m1/s1
    Key: ASJSAQIRZKANQN-UHNVWZDZBB
  • hemiacetal: InChI=1/C5H10O4/c6-2-4-3(7)1-5(8)9-4/h3-8H,1-2H2/t3-,4+,5?/m1/s1
    Key: PDWIQYODPROSQH-OVEKKEMJBQ
  • hemiacetal: InChI=1S/C5H10O4/c6-2-4-3(7)1-5(8)9-4/h3-8H,1-2H2/t3-,4+,5?/m1/s1
    Key: PDWIQYODPROSQH-OVEKKEMJSA-N
  • O=CC[C@@H](O)[C@@H](O)CO
  • hemiacetal: OC[C@@H]1OC(O)C[C@H]1O
Properties
C5H10O4
Molar mass 134.131 g·mol−1
Appearance White solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

l-Deoxyribose can be synthesized from d-galactose.[1] It has been used in chemical research, e.g. in the synthesis of mirror-image DNA.[2]

References edit

  1. ^ , SHI Zhen-Dan, YANG Bing-Hui, and WU Yu-Lin (2002), A stereospecific synthesis of L-deoxyribose, L-ribose and L-ribosides. Tetrahedron, volume 58, issue 16, pp. 3287–3296
  2. ^ Hidehito Urata, Emiko Ogura, Keiko Shinohara, Yoshiaki Ueda and Masao Akagi (1992), Synthesis and properties of mirror-image DNA. Nucleic Acids Research, volume 20 issue 13, pp. 3325–3332