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Preparation of 12‐ and 16‐Membered Macrolactones (Oligolides) from ( S )‐Malic Acid – Low Molecular‐Mass Analogs of the Biopolymer Poly[( S )‐Malic Acid] (PMA)
Author(s) -
Hoffmann Torsten,
Seebach Dieter
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619960806
Subject(s) - malic acid , biopolymer , chemistry , hydroxymethyl , tris , yield (engineering) , biomolecule , carboxylic acid , organic chemistry , carboxylate , polymer chemistry , polymer , biochemistry , citric acid , materials science , metallurgy
As model compounds of uniform composition for the biopolymer PMA, 12‐ and 16‐membered oligolides derived from malic acid by esterification between the carboxylic acid and the β‐hydroxy groups were prepared (Schemes 1 and 2). A reduced form of the triolide derivatives 2, 4 , the tris(hydroxymethyl) triolide 10 , was also synthesized (Scheme 3). The macrocyclic compounds were isolated in up to 60% yield and fully characterized. The water‐soluble tri‐ and tetracarboxylic acids of this type, thus available for the first time, will be studied as potential binders to polycationic biomolecules.