Biochem/physiol Actions
Cis-4-Hydroxy-D-proline may be used as a starting material for the 13-step synthesis of new conformationally restricted PNA adenine monomer and the synthesis of N-Benzyl pyrrolidinyl sordaricin derivatives. Cis-4-Hydroxy-D-proline is a substrate that may be used to study the specificity and kinetics of D-alanine dehydrogenase. Cis-4-Hydroxy-D-proline may be used to analyze the substrate specificity of amino acid transporter PAT1.
Synthesis
General procedure for the synthesis of cis-4-hydroxy-D-proline using L-hydroxyproline as starting material: a synthetic route has been successfully developed for the other two stereoisomers in the pro4 monomer class. A controlled differential isomerization strategy [34] was employed to convert 30 g of trans-4-hydroxy-(L)-proline 5 into its diastereoisomer cis-4-hydroxy-(D)-proline 14 in 57% isolated yield. Further processing of the intermediate by the synthetic method described in Scheme 1 allowed the synthesis of two additional enantiomers of the pro4 structural unit class 3, pro4(2R,4R) and pro4(2R,4S) (see Scheme 3 for details).
References
[1] Tetrahedron Asymmetry, 2003, vol. 14, # 20, p. 3141 - 3152
[2] Tetrahedron Asymmetry, 2002, vol. 13, # 2, p. 197 - 201
[3] Tetrahedron, 2009, vol. 65, # 4, p. 862 - 876
[4] Patent: US2004/77879, 2004, A1. Location in patent: Page 13
[5] Patent: WO2018/13867, 2018, A1. Location in patent: Paragraph 339
