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Literature DB >> 20045977

Synthesis and configurational stability of (S)- and (R)-deuteriothalidomides.

Takeshi Yamamoto¹, Etsuko Tokunaga, Shuichi Nakamura, Norio Shibata, Takeshi Toru.

Abstract

3'-Deuteriothalidomide was synthesized and found to be configurationally five times more stable than thalidomide toward racemization at physiological pH.

Entities: Chemical

Mesh：

Substances：

Year: 2010 PMID： 20045977 DOI： 10.1248/cpb.58.110

Source DB: PubMed Journal: Chem Pharm Bull (Tokyo) ISSN： 0009-2363 Impact factor: 1.645

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Cited

6 in total

1. Differentiation of antiinflammatory and antitumorigenic properties of stabilized enantiomers of thalidomide analogs.

Authors: Vincent Jacques; Anthony W Czarnik; Thomas M Judge; Lex H T Van der Ploeg; Sheila H DeWitt
Journal: Proc Natl Acad Sci U S A Date: 2015-03-09 Impact factor: 11.205

2. Self-disproportionation of enantiomers of thalidomide and its fluorinated analogue via gravity-driven achiral chromatography: mechanistic rationale and implications.

Authors: Mayaka Maeno; Etsuko Tokunaga; Takeshi Yamamoto; Toshiya Suzuki; Yoshiyuki Ogino; Emi Ito; Motoo Shiro; Toru Asahi; Norio Shibata
Journal: Chem Sci Date: 2014-10-30 Impact factor: 9.825

Synthesis and configurational stability of (S)- and (R)-deuteriothalidomides.

1. Differentiation of antiinflammatory and antitumorigenic properties of stabilized enantiomers of thalidomide analogs.

2. Self-disproportionation of enantiomers of thalidomide and its fluorinated analogue via gravity-driven achiral chromatography: mechanistic rationale and implications.

3. Structural basis of thalidomide enantiomer binding to cereblon.

Review 4. The self-disproportionation of enantiomers (SDE): a menace or an opportunity?

5. Preparation of Deuterium Labeled Compounds by Pd/C-Al-D₂O Facilitated Selective H-D Exchange Reactions.

6. Understanding the Thalidomide Chirality in Biological Processes by the Self-disproportionation of Enantiomers.

Synthesis and configurational stability of (S)- and (R)-deuteriothalidomides.

1. Differentiation of antiinflammatory and antitumorigenic properties of stabilized enantiomers of thalidomide analogs.

2. Self-disproportionation of enantiomers of thalidomide and its fluorinated analogue via gravity-driven achiral chromatography: mechanistic rationale and implications.

3. Structural basis of thalidomide enantiomer binding to cereblon.

Review 4. The self-disproportionation of enantiomers (SDE): a menace or an opportunity?

5. Preparation of Deuterium Labeled Compounds by Pd/C-Al-D2O Facilitated Selective H-D Exchange Reactions.

6. Understanding the Thalidomide Chirality in Biological Processes by the Self-disproportionation of Enantiomers.

5. Preparation of Deuterium Labeled Compounds by Pd/C-Al-D₂O Facilitated Selective H-D Exchange Reactions.