Amino Acids, Peptides and Proteins (SPR Amino Acids, by John S. Davies

By John S. Davies

Quintessential reference resource for researchers within the pharmaceutical and allied industries, and on the biology/chemistry interface in academia. summary: quintessential reference resource for researchers within the pharmaceutical and allied industries, and on the biology/chemistry interface in academia. learn more...

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Additional info for Amino Acids, Peptides and Proteins (SPR Amino Acids, Peptides, and Proteins (RSC)) (Vol 36)

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These ligands have found wide-spread applications in transition metal catalyzed asymmetric transformations. The metal–phosphorous bond are often stronger for phosphinites compared to the related phosphines due to the presence of the electron-withdrawing P—OR group. In addition, the empty s*-orbital of the phosphinite P(OR)R2 is stabilized and thus a better acceptor. The preparation of a series of the naturally occurring L-hydroxy-amino acid derived diphenylphosphinites (Boc-Ser(OPPh2)-OMe, Boc-Thr(OPPh2)-OMe, Boc-Tyr(OPPh2)-OMe, Z-Ser (OPPh2)-OMe, and Z-b-Ala-Tyr(OPPh2)-OMe) has been reported from commercially available amino acid precursors.

G. by metal-catalyzed cyclopropanations or carbene addition reactions. An approach based on the Michael-induced ring closure concept led to the desired cyclopropylic compounds by using lithium enolates of phenylimino Gly esters as nucleophiles. These Gly synthons react with a wide range of acceptorsubstituted unsaturated systems. 93 It has been shown that Zn-chelated amino acid ester enolates are highly efficient nucleophiles for stereoselective Michael additions. Subsequent cyclizations provide interesting constrained amino acids (Scheme 21) in high yield and excellent stereoselectivity.

87 The rearrangement could be suppressed by using a more reactive electrophile or the N-Z instead of the N-benzoyl protecting group, and the required (R)-a-benzyl-Met was obtained in 78% yield and in an enantiomeric ratio 90:10. Arylglycines constitute an important class of non-proteinogenic a-amino acids. Unlike other amino acids, which can be effectively prepared in enantiomerically pure form, the apparent simplicity of the aryl-Gly structure is complicated by the ease of racemization at the a-stereocenter.

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