Chemical Properties
White to off-white powder
Occurrence
D-proline is an isomer of the naturally occurring amino acid, L-Proline. D-amino acids have been found in relatively high abundance in human plasma and saliva. These amino acids may be of bacterial origin, but there is also evidence that they are endogenously produced through amino acid racemase activity.
Uses
proline is a skin-conditioning agent. An amino acid found in the collagen molecule.
Uses
Used in the synthesis of (R)-(+)-N-Boc-Pipecolic Acid, (S)-(-)-Coniine, (S)-(+)-Pelletierine, (+)-.beta.-Conhydrine, and (S)-(-)-Ropivacaine and formal synthesis of (-)-Lasubine II and (+)-Cermizine C.
Uses
Labelled D-Proline
Lasubine II and (+)-Cermizine C.
Definition
ChEBI: D-proline is the D-enantiomer of proline. It has a role as a mouse metabolite. It is a D-alpha-amino acid and a proline. It is a conjugate base of a D-prolinium. It is a conjugate acid of a D-prolinate. It is an enantiomer of a L-proline. It is a tautomer of a D-proline zwitterion.
reaction suitability
reaction type: solution phase peptide synthesis
Synthesis
D-amino acids are an important class of chiral reagents and chiral intermediates. Currently, most of the D-amino acids are produced by synthesizing the racemates and then splitting them to obtain the optical isomers. The asymmetric conversion method, using (2 R,3R)-tartaric acid as the splitting agent and in the presence of butyraldehyde, allowed the simultaneous reaction of the racemization of L-proline and the salt crystallization of D-proline with (2 R,3R)-tartaric acid. The total yield was 82 %.
