Open AccessBildung 12- bis 40-gliedriger Oligolide aus enantiomerenreinen 3-Hydroxybuttersäure-Derivaten – Bausteine für eine 2₁- und eine 3₁-Helix
Author(s) -
HansMartin Müller,
M. Dobler,
Peter Zbinden,
Dieter Seebàch
Publication year - 1991
Publication title -
chimia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.387
H-Index - 55
eISSN - 2673-2424
pISSN - 0009-4293
DOI - 10.2533/chimia.1991.376
Subject(s) - tetramer , trimer , helix (gastropod) , chemistry , stereochemistry , catalysis , crystal structure , crystallography , dimer , biology , organic chemistry , ecology , snail , enzyme
Trimeric, tetrameric, and pentameric oligolides are formed preferentially from (S)-βbutyrolactone, or from methyl (R)-3-hydroxybutanoate, upon prolonged treatment with catalytic amounts of tetraoxadistannacyclodecane (Shanzer's macrolactonization catalyst) in refluxing xylene. The crystal structure of the tetramer is described. Substructures of the larger folded oligolides are used for the construction of a left-handed 21-helix, as found in the biopolymer PHB, and a heretofore unknown right-handed 31-helix.