An efficient and enantioselective synthesis of suitably protected beta-[1-(4-malonyl)naphthyl]-L-alanine and beta-[1-(4-malonylmethyl)naphthyl]-L-alanine: Novel fluorescent and non-hydrolysable phosphotyrosine mimetics

作者：Chen Huixiong; Luzy Jean Philippe; Gresh Nohad; Garbay Christiane^*

来源：European Journal of Organic Chemistry, 2006, 2006(10): 2329-2335.

DOI：10.1002/ejoc.200500835

• amino acids
• bioorganic chemistry
• enantioselectivity
• fluorescence

Molecular dynamics simulations based on the structure of the Grb7 SH2 domain in complex with the ErbB2 phosphorylated peptide pTyr1139 have suggested that beta-[1-(4-malonyl)naphthyl]-(L)-alanine (L-mNal) may be accommodated in the pTyr binding pocket and offer additional beneficial interactions. Therefore, this compound and its analog beta-[1-(4-malonylmethyl)naphthyl]-(L)-alanine (L-mmNal), which are new non-hydrolys able phosphotyrosine mimetics, have been prepared by the catalytic asymmetric hydrogenation of the corresponding prochiral enamides with excellent enantioselectivities. These compounds and their dehydro derivatives show interesting fluorescent properties.

• 出版日期2006-5-12