Synthesis of a polyether containing pendant oxirane rings. Regioselectivity of a chair type organozinc complex

Murouchi, Satoshi; Hasebe, Yoshihiro; Tsuruta, Teiji

doi:10.1002/marc.1990.030110304

Cited by 3 publications

References 6 publications

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Polyethers, Propylene Oxide Polymers

Gagnon

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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Propylene oxide and other epoxides under go homopolymerization to form polyethers. In industry the polymerization is started with multifunctional compounds to give a polyether structure having hydroxyl end groups. The hydroxyl end groups are utilized in a polyurethane forming reaction. This article is mainly concerned with propylene oxide and its various homopolymers that are used in the urethane industry. The polymerization of propylene oxide can be catalyzed by base (used commercially), acid (for glycol synthesis), and by coordination catalysts containing Al, Zn, or Fe as the central atom. The mechanism of base‐catalyzed polymerization is reviewed. The physical properties of poly(propylene oxide) as well as the physical methods for determining them are reviewed. Particular emphasis is placed on nmr which has yielded a wealth of information about the structure of poly(propylene oxide) and copolymers of propylene oxide and ethylene oxide.

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Polyethers, Propylene Oxide Polymers

Gagnon

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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Stereochemical behavior of oxirane and bioxirane in their polymerizations initiated with an organozinc complex having chair‐type structure

Tsuruta

1991

Makromolekulare Chemie. Macromolecular Symposia

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A well‐defined organozinc complex, [MeOCH2CH(Me)OZn‐OCH(Me)CH2OMe]2[EtZnOCH(Me)CH2OMe]2 ([Zn‐MP]2, 2), is a very unique and versatile initiator for polymerization of oxirane and bioxirane. [Zn‐MP]2, 2 induced “pure” isospecific polymerization of tert‐butylethylene oxide. The two to two complex, however, became a syndiospecific initiator for cis‐α, β‐disubstituted oxirane. Regioselective nature of [ZnMP]2, 2 complex against bioxirane made it possible to prepare a soluble polyether having pendant oxirane rings.

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Copolymers of lysine and polyethylene glycol: a new family of functionalized drug carriers

Nathan

Zalipsky²,

Ertel³

et al. 1993

Bioconjugate Chem.

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Poly(PEG-Lys), a new, water-soluble poly(ether urethane), derived from L-lysine and poly(ethylene glycol) was investigated as a precursor for the preparation of polymeric drug conjugates. To facilitate a wide variety of coupling chemistries, the pendent carboxyl groups of poly(PEG-Lys) were converted to other reactive functional groups (amino, hydroxyl, active ester, and aldehyde) in high yield. These reactive pendent chains were then used as anchors for the covalent attachment of penicillin V and cephradine, two clinically used antimicrobial agents. Coupling to the carrier was achieved in good yields and the chemical versatility of this system was demonstrated by the preparation of conjugates having antibiotic ligands linked via biostable or biodegradable linkages to the carrier, either directly or via a spacer. Conjugate 4, poly(PEG-Lys-penicillin V ester), was obtained by linking penicillin V to the polymer backbone via hydrolytically labile ester bonds. This conjugate exhibited activity similar to that of the parent drug against three clinically important strains of bacteria. Drug activity coincided with the release of the drug from the carrier. Hydrolytically stable cephradine-containing conjugates were prepared by three different coupling methods but showed no antibiotic activity. 14C-labeled poly(PEG-Lys) was injected into mice and its biodistribution was monitored for 48 h. The carrier showed no preferential uptake by liver, spleen, or kidney. No signs of acute toxicity were evident in mice or rats when poly(PEG-Lys) was administered iv and ip at doses up to 10 g/kg. These results indicate that poly(PEG-Lys) is a promising precursor for the preparation of soluble drug conjugates.

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Synthesis of a polyether containing pendant oxirane rings. Regioselectivity of a chair type organozinc complex

Cited by 3 publications

References 6 publications

Polyethers, Propylene Oxide Polymers

Polyethers, Propylene Oxide Polymers

Stereochemical behavior of oxirane and bioxirane in their polymerizations initiated with an organozinc complex having chair‐type structure

Copolymers of lysine and polyethylene glycol: a new family of functionalized drug carriers

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