Homochiral oligopeptides generated via an asymmetric induction in racemic 2D crystallites at the air-water interface; the system ethyl/thio-ethyl esters of long-chain amphiphilic alpha-amino acids.
N(epsilon)-stearoyl-lysine-ethyl-ester (C18-OE-Lys) operates as an efficient desymmetrizing agent for the generation of homochiral oligopeptides via a reaction catalyzed by silver ions in two-dimensional (2D) quasi-racemic crystallites of the corresponding thio-ester (C18-TE-Lys) self-assembled on water.
Rubinstein
Irina
I
Department of Material and Interfaces, The Weizmann Institute of Science, 76100-Rehovot, Israel.
Kjaer
Kristian
K
Weissbuch
Isabelle
I
Lahav
Meir
M
D000596:Amino Acids / Q000737:chemistry*; D004951:Esterification; D057927:Hydrophobic and Hydrophilic Interactions; D007477:Ions / Q000737:chemistry; D015394:Molecular Structure; D009842:Oligopeptides / Q000737:chemistry*; D044367:Phase Transition; D012834:Silver / Q000737:chemistry; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D014867:Water / Q000737:chemistry*; D014961:X-Ray Diffraction
D000596:Amino Acids; D007477:Ions; D009842:Oligopeptides; D013438:Sulfhydryl Compounds; D014867:Water; D012834:Silver