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Synthesis of proline-derived dipeptides and their catalytic enantioselective direct aldol reactions: catalyst, solvent, additive and temperature effects.
Amino Acids. 2010 Mar; 38(3):839-45.AA

Abstract

A series of dipeptides of L-proline-L-amino acid and L-proline-D-amino acid were synthesized to evaluate the catalytic effect for asymmetric direct aldol reactions. In the direct aldol reaction, a catalyst of L-proline-L-amino acid achieves better enantioselectivity than the corresponding L-proline-D-amino acid catalyst. Solubility of the dipeptide catalysts in the solvents is a key point for achieving a better yield of the direct aldol reaction, while hydrogen bonding of solvent does not play an important role in attaining better enantioselectivity and yield. Yield and enantioselectivity of the direct aldol reaction in water were improved by NMM and SDS additives, but the results that were done in plain DMSO were even better.

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Authors+Show Affiliations

Chen YH
Department of Chemistry, National Cheng Kung University, Tainan, Taiwan, ROC.
Sung PH
No affiliation info available
Sung K
No affiliation info available

MeSH

CatalysisDimethyl SulfoxideDipeptidesHydrogen BondingMagnetic Resonance SpectroscopyProlineSodium Dodecyl SulfateSolubilitySolventsStereoisomerismTemperature

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

19370392

Citation

Chen, Y-H, et al. "Synthesis of Proline-derived Dipeptides and Their Catalytic Enantioselective Direct Aldol Reactions: Catalyst, Solvent, Additive and Temperature Effects." Amino Acids, vol. 38, no. 3, 2010, pp. 839-45.
Chen YH, Sung PH, Sung K. Synthesis of proline-derived dipeptides and their catalytic enantioselective direct aldol reactions: catalyst, solvent, additive and temperature effects. Amino Acids. 2010;38(3):839-45.
Chen, Y. H., Sung, P. H., & Sung, K. (2010). Synthesis of proline-derived dipeptides and their catalytic enantioselective direct aldol reactions: catalyst, solvent, additive and temperature effects. Amino Acids, 38(3), 839-45. https://doi.org/10.1007/s00726-009-0290-3
Chen YH, Sung PH, Sung K. Synthesis of Proline-derived Dipeptides and Their Catalytic Enantioselective Direct Aldol Reactions: Catalyst, Solvent, Additive and Temperature Effects. Amino Acids. 2010;38(3):839-45. PubMed PMID: 19370392.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of proline-derived dipeptides and their catalytic enantioselective direct aldol reactions: catalyst, solvent, additive and temperature effects. AU - Chen,Y-H, AU - Sung,P-H, AU - Sung,Kuangsen, Y1 - 2009/04/17/ PY - 2009/02/07/received PY - 2009/03/31/accepted PY - 2009/4/17/entrez PY - 2009/4/17/pubmed PY - 2010/7/2/medline SP - 839 EP - 45 JF - Amino acids JO - Amino Acids VL - 38 IS - 3 N2 - A series of dipeptides of L-proline-L-amino acid and L-proline-D-amino acid were synthesized to evaluate the catalytic effect for asymmetric direct aldol reactions. In the direct aldol reaction, a catalyst of L-proline-L-amino acid achieves better enantioselectivity than the corresponding L-proline-D-amino acid catalyst. Solubility of the dipeptide catalysts in the solvents is a key point for achieving a better yield of the direct aldol reaction, while hydrogen bonding of solvent does not play an important role in attaining better enantioselectivity and yield. Yield and enantioselectivity of the direct aldol reaction in water were improved by NMM and SDS additives, but the results that were done in plain DMSO were even better. SN - 1438-2199 UR - https://www.unboundmedicine.com/medline/citation/19370392/Synthesis_of_proline_derived_dipeptides_and_their_catalytic_enantioselective_direct_aldol_reactions:_catalyst_solvent_additive_and_temperature_effects_ L2 - https://dx.doi.org/10.1007/s00726-009-0290-3 DB - PRIME DP - Unbound Medicine ER -