Synthesis of enantiomerically pure (2R, 5S)- and (2R, 5R)-5-hydroxypipecolic acid from glycinate Schiff bases

Some of the amino acid chemistry going on in the Laboratory of Amino Acids, Peptides and Proteins

“…We have been able to prepare several optically pure mono and disubstituted a-amino acids (Bajgrowicz et al, 1983;Chaari et al, 1991;Jenhi et al, 1991;Tabcheh et al, 1991;Tabcheh et al, 1992;Hoarau et al, 1996;Jacob et al, 1997;Receveur et al, 1995Receveur et al, , 1998, imino acids (Bajgrowicz et al, 1986) and functionalized amino acids (El Achqar et al, 1988;Tabcheh et al, 1992). The method was extended to the asymmetric synthesis of aminophosphonic acids (Jacquier et al, 1988;Ouazzani et al, 1991;Alami et al, 1992) and of constituents of natural products (Jacquier et al, 1984), including leucinostatine (El Hadrami et al, 1991).…”

Asymmetric syntheses of pipecolic acid and derivatives

“…15). Recently, Hoarau (Hoarau et al, 1996) prepared (R)-homoallyl glycine derivative 58. The key step involves a diastereoselective alkylation of the Schiff base 57 derived from (S,S,S)-2-hydroxypinan-3-one.…”

Significance of the Natural Occurrence of L‐ Versus D‐Pipecolic Acid: A Review

“…L‐pipecolic acid is a precursor of many microbially derived biologically active compounds (Table ). Many studies have also described the synthetic preparation of pipecolic acid derivates including aryl‐ and alkyl‐substituted derivatives, cis ‐ and trans ‐5‐hydroxy‐D‐pipecolic acid from glycinate Schiff bases, C‐3‐, C‐4‐, C‐5‐, and C‐6‐substituted or paramagnetic DL‐pipecolic acid derivatives, or the enantioselective synthesis of 4,5‐dehydropipecolic acid (baikiain) …”

“…Many studies have also described the synthetic preparation of pipecolic acid derivates including aryl-and alkyl-substituted derivatives, cis-and trans-5-hydroxy-D-pipecolic acid from glycinate Schiff bases, C-3-, C-4-, C-5-, and C-6-substituted or paramagnetic DL-pipecolic acid derivatives, or the enantioselective synthesis of 4,5-dehydropipecolic acid (baikiain). [42][43][44][45][46][47] 18 Umair and Simpson, 20 Chang and Adams, 21 Revelles et al, 22 Fujii et al, 23 Tsotsou and Barbirato, 24 Gatto et al, 25 Galili et al 79 ). Higher plants (A); Pseudomonas putida and P. putida KT 2440 (B); Escherichia coli transformed by the lat gene from Flavobacterium lutescens IFO3084 and proC gene from E. coli mutant RK4904 (C); microorganisms transformed by L-lysine cyclodeaminase (E. coli transformed by the SpLCD gene from Streptomyces pristinaespiralis and S. hygroscopicus NRRL 5491 disrupted by rapL gene) (D); animals (E).…”