Water-soluble L-alanine and related oligopeptide conjugates with poly[(R,S)-3-hydroxybutanoic acid] oligomers, synthesis and structural studies by means of electrospray ionization multistage mass spectrometry.
The reactions of (R,S) beta-butyrolactone with L-alanine and related oligopeptides (Ala-Ala-Ala) were investigated. The resulting water-soluble oligomers were composed of poly[(R,S)-3-hydroxybutanoic acid] (a-PHB) covalently conjugated to L-alanine and Ala-Ala-Ala oligopeptide. The other chain end was of the carboxylic acid type. The structure of the obtained oligomers was assessed by electrospray ionization multistage mass spectrometry (ESI-MSn) and the respective structural information was completed by IR, NMR, and GPC analyses. The molecular weight and structure of the products could be controlled through reaction conditions. Using this new synthetic approach. a-PHB oligomers with well-defined end groups, as well as respective block copolymers, can be prepared via regioselective ring-opening oligomerization of (R,S) beta-butyrolactone induced by amino acids under their zwitterionic form.
Arkin
Z G
ZG
Polish Academy of Sciences, Centre of Polymer Chemistry, Zabrze.
Rydz
J
J
Adamus
G
G
Kowalczuk
M
M
D020155:3-Hydroxybutyric Acid / Q000737:chemistry; D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000378:metabolism; D000409:Alanine / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry; D002849:Chromatography, Gas; D006885:Hydroxybutyrates / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009842:Oligopeptides / Q000737:chemistry*; D011091:Polyesters / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D000094122:Polyhydroxybutyrates
D020155:3-Hydroxybutyric Acid; D015107:4-Butyrolactone; D000409:Alanine; D002264:Carboxylic Acids; D006885:Hydroxybutyrates; D009842:Oligopeptides; D011091:Polyesters; C003182:poly-beta-hydroxybutyrate; D000094122:Polyhydroxybutyrates; C013426:beta-butyrolactone