Chemical synthesis and crystallization of the dipeptide AcPheIleNH(2) in TTAB/heptane/octanol reversed micelles.
The chemical synthesis of the dipeptide acetyl phenyl iso-leucin-amide (AcPheIleNH(2)) in tetradecyl trimethyl ammonium bromide (TTAB)/ heptane/octanol/carbonate buffer reversed micelles is described. The co-existence of the surfactant bounded minute water pools within the bulk organic solvent enables the simultaneous solubilization of the polar (IleNH(2)) and apolar (AcPheOEt) substrates, thus enabling the synthesis to take place at the micellar interface. The synthesis was favored by increasing the micellar interface via an increase in water content and surfactant concentration. The best dipeptide yield (87%) was obtained at 32 degrees C, with the largest concentrations of TTAB (200 mM) and water (1100 mM) tested. The low solubility of the dipeptide in the micellar media further led to the formation and growth of needle-like crystals during synthesis, thus enabling the removal of product from solution.
Dias
A I
AI
Centro de Engenharia Biológica e Química, Instituto Superior Técnico, Av. Rovisco Pais, 1049-001 Lisboa, Portugal.
Feliciano
A S
AS
Cabral
J M S
JM
Prazeres
D M F
DM
D003460:Crystallization; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D006536:Heptanes; D007532:Isoleucine / Q000737:chemistry*; D008823:Micelles; D000442:Octanols; D010649:Phenylalanine / Q000737:chemistry*; D050337:Trimethyl Ammonium Compounds
D004151:Dipeptides; D006536:Heptanes; D008823:Micelles; D000442:Octanols; D050337:Trimethyl Ammonium Compounds; D007532:Isoleucine; D010649:Phenylalanine; C009410:tetradecyltrimethylammonium