Synthesis of Silaproline, a New Proline Surrogate

The asymmetric synthesis of a new proline surrogate, incorporating the dimethylsilyl group at position 4 of proline using Schollkopf's bis-lactim ether method, is described.

[1]  A. Mordini,et al.  A stereoselective approach to the synthesis of ?-silylated amino acids , 1998 .

[2]  R. Pascal,et al.  Preservation of the protective group under alkaline conditions by using CaCl2. Applications in peptide synthesis , 1998 .

[3]  M. Sibi,et al.  Synthesis of silicon containing alanines , 1998 .

[4]  B. Badet,et al.  Orthogonally protected imidazolidine-2-carboxylic acid, a new proline surrogate suitable for SPPS , 1998 .

[5]  D. Ryan,et al.  PSEUDO-PROLINES AS A MOLECULAR HINGE : REVERSIBLE INDUCTION OF CIS AMIDE BONDS INTO PEPTIDE BACKBONES , 1997 .

[6]  P. Karoyan,et al.  New strategy for the synthesis of 3-substituted prolines , 1997 .

[7]  M. Mutter,et al.  Pseudo-Prolines as a Solubilizing, Structure-Disrupting Protection Technique in Peptide Synthesis , 1996 .

[8]  D. Cole,et al.  SILICON-CONTAINING AMINO ACIDS AND PEPTIDES. ASYMMETRIC SYNTHESIS OF (TRIALKYLSILYL)ALANINES , 1995 .

[9]  W. Oppolzer,et al.  Asymmetric Alkylations of a Sultam‐Derived Glycine Equivalent: Practical preparation of enantiomerically pure α‐amino acids , 1994 .

[10]  R. Duthaler.  Recent developments in the stereoselective synthesis of α-aminoacids , 1994 .

[11]  R. Sheppard,et al.  Amino acid structure and "difficult sequences" in solid phase peptide synthesis. , 2009, International journal of peptide and protein research.

[12]  M. Mutter,et al.  SERINE DERIVED OXAZOLIDINES AS SECONDARY STRUCTURE DISRUPTING, SOLUBILIZING BUILDING-BLOCKS IN PEPTIDE-SYNTHESIS , 1992 .

[13]  G. I. Tesser,et al.  Enhancement of solubility by temporary dimethoxybenzyl-substitution of peptide bonds. Towards the synthesis of defined oligomers of alanine and of lysyl-glutamyl-glycine. , 2009, International journal of peptide and protein research.

[14]  M. Roumestant,et al.  2-Hydroxy-3-pinamone as chiral auxiliary in the asymmetric synthesis of α-amino acids , 1988 .

[15]  Robert M. Williams,et al.  Asymmetric synthesis of α-amino acids: Comparison of enolate vs. cation functionalization of N-BOC-5, 6-diphenyl-2,3,5,6-tetrahydro-4h-1,4-oxazin-2-ones , 1988 .

[16]  U. Schöllkopf,et al.  Asymmetric Synthesis of Cyclic α‐Amino Acids by the Bislactim Ether Method , 1987 .

[17]  C. Toniolo,et al.  Self-association and solubility of peptides. Solvent-titration study of protected C-terminal segments of porcine secretin. , 2009, International journal of peptide and protein research.

[18]  U. Groth,et al.  Enantioselective Syntheses of (R)‐Amino Acids Using L‐Valine as Chiral Agent , 1981 .