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

CAS Number

18546-37-7^Y

ChemSpider

5362530^N
8031184 hemiacetal^N

Jmol interactive 3D

Image
hemiacetal: Image

PubChem

6994527
9855484 hemiacetal

InChI

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

SMILES

O=CC[C@@H](O)[C@@H](O)CO
hemiacetal: OC[C@@H]1OC(O)C[C@H]1O

Properties

Chemical formula

C₅H₁₀O₄

Molar mass

134.13 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).

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Infobox references

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 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

↑ 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
↑ 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

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