Synthesis of alternating polydepsipeptides by ring‐opening polymerization of morpholine‐2,5‐dione derivatives

Abstract

Polydepsipeptides with alternatiii .a-hydroxy acid and a-amino acid residues were synthesized by ring-opening polymerization 3 I morpholine-2,5-dione derivatives. The polymerizations were performed in the melt using stannous octoate as an initiator. Molecular weights of the polydepsipeptides obtained ranged from 0,9 . lo4 to 1,4 * lo4. Morpholine-2,5-dione derivatives unsubstituted at the &position gave polymers with the highest molecular weights. Poly((S)-alaninealt-glycolic acid) was semi-crystalline,. whereas all other polydepsipeptides synthesized were amorphous. Morphoiine-2,5-dione derivatives were synthesized by N-acylation of glycine, (S)alanine or (5')-valine with chloroacetyl chloride or (R,S)-2-bromopropionyl bromide, followed by ring-closure of N-(2-halogenacyl)-amino acid sodium salts in the melt in 4 to 83% yield. Low yields in the cyclization reaction of N-(2-halogenacyl)-(S)-valine were accompanied by the formation of the corresponding polydepsipeptides in 13 to 46% yield, with molecular weights ranging from 3,3 . 104 to 4,9 -lo4. 0 1990, HUthig & Wepf Verlag, Base1CCC 0025-1 16X/90/$03.00

Synthesis and characterization of new ABA triblock copolymers with poly[3(S)-isobutylmorpholine-2,5-dione] and poly(ethylene oxide) blocks

“…2. IR spectra of the homopolymers PIBMD (1) and PEO6000(2) and the copolymer PIPE1 (3) with the absorption band of the C1O bond in the PIBMD block. Fig.…”

“…The contents of the flask were heated to reflux until no water was formed any more. The resulting solution was cooled to room temperature and washed successively with 26200 mL NaHCO 3 The static contact angle of the copolymers as a film on a glass plate was measured with the contact angle system G40 (Krüss GmbH) at room temperature.…”

“…Many researchers studied the ring-opening polymerization of different morpholine-2,5-dione derivatives [2][3][4][5] . The copolymerization of morpholine-2,5-diones with D,L-lactide (DLLA), glycolide (GA), or e -caprolactone (CL) yields poly(ester-amides) with a variety of properties [6][7][8] .…”

Enzyme-catalyzed ring-opening polymerization of 3(S)-isopropylmorpholine-2,5-dione

“…Many researchers studied the ring-opening polymerization of different morpholine-2,5-dione derivatives [2][3][4][5] in the presence of Sn(Oct) 2 as a catalyst. The copolymerization of morpholine-2,5-diones with D,L-lactid (DLLA), glycolid (GA) or e-caprolactone (CL) produces poly-(esteramides) with a variety of properties [6][7][8] .…”

Progress in Depsipeptide‐Based Biomaterials

“…Polydepsipeptides have recently attracted much attention and already show great promise for biomedical applications such as tissue engineering and drug delivery. Quite a few polydepsipeptides – including several with pendant functional groups, such as carboxylic, hydroxyl, amine and thiol groups – have been synthesized and their applications explored 13, 14. Polydepsipeptide‐based copolymers including random,15 block,16 multiblock17 and graft copolymers18 were also investigated.…”