Synthesis of polyamides from active O,O′‐diacyl derivatives of N‐hydroxy compounds and diamines under mild conditions

U n i v e r s i t y o f Michigan, Ann Arbor, M I USA 48109 V i c t o r P. Chu, present address Abbott Laboratories, D-gOU, AP3B, North Chicago, I L 60064 A b s t r a c t -Poly(N-acyl ethylenimine) o f v a r i o u s molecular weights was synthesized by t h e c a t i o n i c ring-opening p o l y m e r i z a t i o n o f 2-H-2-oxazoline and 2-methyl-2-oxazoline. a f f o r d e d t h e l i n e a r poly(ethy1enimine) which was used i n t h e f o l l o w i n g g r a f t i n g r e a c t i o n s . Vapor pressure osmometry, g e l permeation chromatography and v i s c o s i t y measurements were used t o c h a r a c t e r i z e t h e polymers synthesized. Potassium 2-(cytos-1 -yl )propanoate and potassium 3-(cytos-1 -yl )butanoate were synthesized i n good y i e l d from t h e n u c l e i c a c i d base. These c y t o s y l pendant groups were g r a f t e d onto t h e p o l y ( e t h y 1 -enimi ne) u s i n g 4-chl oro-1-(4-chlorobenzenesul f o n y l ) b e n z o t r i azole, 90% g r a f t , and norborn-5-ene-2.3-carboximido diphenyl phosphate, 70% g r a f t . G r a f t i n g o f t h e 2-butoxycarbonyl and -n-butoxycarbonyl p r o t e c t e d c y t o s y l pendant groups r e s u l t e d i n a 47% g r a f t . Hypochromicity s t u d i e s i n d i c a t e d an ordered s t r u c t u r e a t t h e l o c a l l e v e l . The secondary s t r u c t u r e i s a base-stacked conformation. L i g h t s c a t t e r i n g r e s u l t s gave i n s i g h t i n t o t h e t e r t i a r y s t r u c t u r e o f t h e macromolecule. polymer e x i s t s i n s o l u t i o n as s t i f f chains, r o d -l i k e i n nature. Continuous m i x i n g experiments were c a r r i e d o u t w i t h p o l y r i b onucleotides. The Job p l o t s i n d i c a t e d increased l e v e l o f ordered conformation w i t h e i t h e r an increase i n t h e molecular weight o r an increase o f t h e base t o base d i s t a n c e i n t h e analog.

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Nucleic acid base grafted poly(ethylenimine): Polynucleotide analog and therapeutic agent

Overberger

Chu

1985

Makromol. Chem.

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Studies of some bioactive N‐p‐methacrylamidobenzoic esters

Yang

Leng

et al. 1981

J. Polym. Sci. Polym. Chem. Ed.

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Preparations of four typical bioactive esters of N‐p‐methacrylamidobenzoic monomers and their reactive polymers as immobilized trypsin carriers are described. N‐p‐methacrylamidobenzoic active ester monomers containing COONB, COOSu, COOObt, or COOBT group can react with an aliphatic amine such as benzylamine at room temperature to give an identical product, N‐benzyl‐p‐methacrylamidobenzamide. However, only monomers with COOObt or COOBT group can also react with an aromatic amine such as aniline to give N‐phenyl‐p‐methacrylamidobenzamide. These monmoers polymerized readily in solution with azobisisobutyronitrile as free‐radical initiator; the polymers were used to immobilize trypsin. Among the four different active esters for the immobilization of trypsin, thE HONB and HOSu active ester showed rather higher bioactivities than the HOObt or HOBT active ester under the same conditions. Both P(MABONB)‐trypsin and P(MABOSu)‐trypsin matrices possess higher biological activities by about four or three times that of P(MABOObt)‐trypsin or P(MABOBT)‐trypsin matrices, respectively. It is proposed that these rather high bioactivities may be attributed to the “specific” aminolysis of reactive polymer with COONB or COOSu active ester group by aliphatic amino substituents.

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Synthesis of polyamides from active 4,4′‐diacylbis‐2‐aryl‐1,3,4‐oxadiazoline‐5‐thiones and ‐ones and diamines under mild conditions

Saegusa

Nakamura

Chau

et al. 1983

J. Polym. Sci. Polym. Chem. Ed.

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SynopsisNew active bisamides, 4,4'-diacylbis-2-aryl-1,3,4-oxadiazoline-5-thiones and -ones having various electron accepting groups in the oxadiazoline units were synthesized, and their reactivities toward diamines were investigated. The polycondensation reactions of the bisamides derived from 2aryl-1,3,4-oxadiazoline-5-thiones with both aliphatic and aromatic diamines occurred rapidly even a t room temperature to form high-molecular-weight polyamides in quantitative yields. The reactivities of the bisamides having electron accepting groups such as p-chloro and p-nitro groups, particularly p-nitro groups, toward diamines were much higher than that of the corresponding bisamide having no such group. It was also found that reaction conditions such as solvent, monomer concentration, and temperature bad a strong influence on the molecular weight of the resulting polyamides. Aminolysis of several benzoyl derivatives of 2-aryl-1,3,4-oxadiazoline-5-thiones and -ones was also carried out as a model reaction, and the effect of electron accepting groups on the reactivity of these compounds was discussed.

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Synthesis of polyamides from active O,O′‐diacyl derivatives of N‐hydroxy compounds and diamines under mild conditions

Cited by 16 publications

References 7 publications

Nucleic acid base grafted poly(ethylenimine): Polynucleotide analog and therapeutic agent

Nucleic acid base grafted poly(ethylenimine): Polynucleotide analog and therapeutic agent

Studies of some bioactive N‐p‐methacrylamidobenzoic esters

Synthesis of polyamides from active 4,4′‐diacylbis‐2‐aryl‐1,3,4‐oxadiazoline‐5‐thiones and ‐ones and diamines under mild conditions

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