Construction of chiral polyesters from polycondensation of multifunctional monomer containing both flexible amino acid and rigid pendant groups with aromatic diols

Amino Acids

Volumn 39, Issue 3, 2010, Pages 841-848

  Mallakpour, Shadpour ^a   Khani, Marziyeh ^a  

^a ISFAHAN UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

Inherent viscosity; Isoleucine; Optically active polymers; Polycondensation; Polyesters

Indexed keywords

1 METHYL 2 PYRROLIDINONE; 5 (3 METHYL 2 PHTHALIMIDYLPENTANOYLAMINO)ISOPHTHALIC ACID; AMINO ACID; CHLORIDE; GLYCOL; ISOPHTHALIC ACID; MONOMER; N,N DIMETHYLACETAMIDE; N,N DIMETHYLFORMAMIDE; NITROGEN; PHTHALIMIDE; POLYESTER; PYRIDINE; SOLVENT; TOSYLCHLORIDE; UNCLASSIFIED DRUG; POLYCYCLIC AROMATIC HYDROCARBON; POLYMER;

ARTICLE; BIODEGRADABILITY; CHIRALITY; CONTROLLED STUDY; DISSOLUTION; ESTERIFICATION; INFRARED SPECTROSCOPY; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SOLUBILITY; TEMPERATURE; THERMOGRAVIMETRY; THERMOSTABILITY; VISCOSITY; CHEMICAL STRUCTURE; CHEMISTRY;

AMINO ACIDS; MOLECULAR STRUCTURE; POLYCYCLIC HYDROCARBONS, AROMATIC; POLYESTERS; POLYMERS; SOLUBILITY; THERMOGRAVIMETRY;

EID: 77956942882     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-010-0539-x     Document Type: Article

References (43)

1. Bajgai MP, Aryal S, Lee DR, Park SJ, Kim HY (2008) Physico-chemical characterization of self-assembled poly(ε-caprolactone) grafted dextran nanoparticles. Colloid Polym Sci 286:517-524
2. Barroso MN, Cerutti ES, Rodriguez AM, Jauregui EA, Farkas O, Perczel A, Enriz RD (2001) Side-chain conformations for selected backbone conformations of N-acetyl-L-isoleucine-N-methylamide and N-acetyl-L-nor-isoleucine-N-methylamide. An exploratory ab initio study. J Mol Struct (Theochem) 548:21-37 (Pubitemid 32678497)
3. Bikiaris DN, Achilias DS (2008) Synthesis of poly(alkylene succinate) biodegradable polyesters, Part II: mathematical modelling of the polycondensation reaction. Polymer 49:3677-3685
4. Bordes P, Pollet E, Averous L (2009) Nano-biocomposites: biodegradable polyester/nanoclay systems. Prog Polym Sci 34:125-155
5. Bucio E, Fitch JW, Venumbaka SR, Cassidy PE (2005) Synthesis and properties of aliphatic spirodilactam diphenol containing polyesters. Polymer 46:3971-3974
6. Chen J, Zhou Y, Nan Q, Ye X, Sun Y, Zhang F, Wang Z (2007) Preparation and properties of optically active polyurethane/TiO2 nanocomposites derived from optically pure 1, 1'-binaphthyl. Eur Polym J 43:4151-1159
7. Doi M, Yamaoka I, Fukunaga T, Nakayama M (2003) Isoleucine, a potent plasma glucose lowering amino acid, stimulates glucose uptake in C2C12 myotubes. Biochem Biophys Res Commun 312:1111-1117
8. Edlund U, Albertsson AC (2003) Polyesters based on diacid monomers. Adv Drug Deliver Rev 55:585-609
9. Feldman D, Barbalata A (1996) Synthetic polymers, technology, properties, applications. Chapman and Hall, London
10. Ferrero E, Espeso JF, Campa JGDL, Abajo JD, Lozano AE (2002) Synthesis and characterization of aromatic polyamides containing alkylphthalimido pendent groups. J Polym Sci Part A Polym Chem 40:3711-3724
11. Flores A, Balta Calleja FJ (1998) Mechanical study of sintered aromatic polyesters as revealed by microindentation measurements. J Mater Sci 33:3567-3571
12. Higashi F, Tobe A (2001) A new polycondensation involving dicarboxylic acids with differently activated carboxyl groups by TsCl/DMF/Py. Macromol Chem Phys 202:745-749
13. Hwang KJ, Park JW, Kim I, Ha CS (2006) Effect of a compatibilizer on the microstructure and properties of partially biodegradable LDPE/aliphatic polyester/organoclay nanocomposites. Macromol Res 14:179-186
14. Itsuno S (2005) Chiral polymer synthesis by means of repeated asymmetric reaction. Prog Polym Sci 30:540-558
15. Kawabe M, Sano M, Hagiwara A, Tamano S, Suzuki S, Shirai T (2006) Lack of carcinogenicity of L-isoleucine in F344/DuCrj rats. Food Chem Toxicol 44:278-285 (Pubitemid 41773822)
16. Khang G, Rhee JM, Jeong JK, Lee JS, Kim MS, Cho SH, Lee HB (2003) Local drug delivery system using biodegradable polymers. Macromol Res 11:207-223
17. Kini AK, Farokhi SA, Nandibewoor ST (2002) A comparative study of ruthenium(III) catalysed oxidation of L-leucine and L-isoleu-cine by alkaline permanganate. A kinetic and mechanistic approach. Transit Metal Chem 27:532-540
18. Koyama E, Sanda F, Endo T (1997) Polycondensations of hydroxy-carboxylic acids derived from optically active aminoalcohols and acid anhydrides-syntheses of functional poly(ester-amide)s. J Polym Sci Part A Polym Chem 35:345-352
19. Kumar R, Tyagi R, Parmar VS, Samuelson LA, Kumar J, Watterson AC (2003) Enzymatic synthesis of multi-component copolymers and their structural characterization. Mol Divers 6:287-295
20. Liaw DJ, Chen PS (1996) Preparation and properties of polyesters derived from 4, 4'-sulfonyl dibenzoyl chloride by solution polycondensation. J Polym Sci Part A Polym Chem 34:885-891
21. Liaw DJ, Hsu JJ, Liaw BY (2001) Synthesis and characterization of new soluble cardo polyesters derived from 1, 1-bis-[4-(4-chlorocarboxyphenoxy) phenyl]-4-tert-butylcyclohexane with various bisphenols by solution polycondensation. J Polym Sci Part A Polym Chem 39:2951-2956
22. Liaw DJ, Fan CL, Lin CC, Wang KL (2004) Synthesis and characterization of new soluble poly(esterimide)s containing noncoplanar 2, 2'-dimethyl-4, 4'-biphenylene unit. J Appl Polym Sci 92:2486-2493
23. Mallakpour S, Khani M (2007) Novel optically active poly(amide-imide)s derived from N-trimellitylimido-L-isoleucine and different diisocyanates. Polym Bull 59(5):587-596
24. Mallakpour S, Kolahdoozan M (2006) Preparation and characterization of novel optically active poly(amide-ester-imide)s based on bis(p-aminobenzoic acid)-N-trimellitylimido-S-valine via direct polyesterification. Iran Polym J 15:307-315 (Pubitemid 44020741)
25. Mallakpour S, Sepehri S (2008) Synthesis and characterization of new optically active polyesters by step-growth polymerization of novel aromatic (2S)-4-[(4-methyl-2-phthalimidyl-pentanoylamino)ben-zoylamino]isophthalic acid with aromatic diols. J Appl Polym Sci 110(5):2942-2949
26. Mallakpour S, Seyedjamali S (2008) Synthesis and characterization of novel organosoluble and optically active aromatic polyesters containing L-methionine and phthalimide pendent groups. Amino Acids 34(4):531-538
27. Mallakpour S, Seyedjamali H (2009) Fast synthesis of optically active polyamides containing L-methionine linkages in ionic liquid via a microwave-assisted process. Colloid Polym Sci 287:1111-1116
28. Mallakpour S, Taghavi M (2008) A facile, microwave-assisted synthesis of novel optically active polyamides derived from 5-(3-methyl-2- phthalimidylpentanoylamino) isophthalic acid and different diisocyanates. Eur Polym J 44:87-97
29. Mallakpour S, Zadehnazari A (2010) Microwave irradiation as a versatile tool for increasing reaction rates and yields in synthesis of optically active polyamides containing flexible L-leucine amino acid. Amino Acid (in press)
30. Mamer OA (2001) Initial catabolic steps of isoleucine, the R-pathway and the origin of alloisoleucine. J Chromatogr B 758:49-55
31. Murin R, Mohammadi G, Leibfritz D, Hamprecht B (2009) Glial metabolism of isoleucine. Neurochem Res 34:194-204
32. Odian G (2004) Principles of polymerization. Wiley Interscience, New York
33. Okada M (2002) Chemical syntheses ofbiodegradable polymers. Prog Polym Sci 27:87-133
34. Okamoto Y, Nakano T (1994) Asymmetric polymerization. Chem Rev 94:349-372
35. Pan P, Inoue Y (2009) Polymorphism and isomorphism in biodegradable polyesters. Prog Polym Sci 34:605-640
36. Peng Z, Fang J, Li J, Liu L, Du G, Chen J, Wang X, Ning J, Cai L (2009) Combined dissolved oxygen and pH control strategy to improve the fermentative production of L-isoleucine by Brevi-bacterium lactofermentum. Bioprocess Biosyst Eng (in press)
37. Sahm H, Eggeling L, Morbach S, Eikmanns B (1999) Construction of L-isoleucine overproducing strains of Corynebacterium glutam-icum. Naturwissenschaften 86:33-38
38. Samui AB, Ratna D, Chavan JG, Deb PC (2002) Modification of epoxy resin with optically active carboxylic acid. J Appl Polym Sci 86:2523-2529
39. Sava I, Iosip MD, Bruma M, Hamciuc C, Robison J, Okrasa L, Pakula T (2003) Aromatic polyamides with pendent acetoxybenzamide groups and thin films made therefrom. Eur Polym J 39:725-738
40. Tamami B, Yeganeh H, Kohmareh GA (2004) Synthesis and characterization of novel polyesters derived from 4-aryl-2, 6-bis(4-chlorocarbonyl phenyl) pyridines and various aromatic diols. Eur Polym J 40:1651-1657
41. Tawfik SY, Asaad JN, Sabaa MW (2003) Effect of polyester backbone structure on the cured products properties. Polym Test 22:747-759
42. Vijayakumar CT, Sivasamy P, Rajkumar T (2007) Synthesis and characterization of 1, 3-bis(2-hydroxyethoxy) benzene based saturated and unsaturated polyesters. Eur Polym J 43:3028-3035
43. Zhang S, Li Y, Yin D, Wang X, Zhao X, Shao Y, Yang S (2005) Study on synthesis and characterization of novel polyimides derived from 2, 6-bis(3-aminobenzoyl) pyridine. Eur Polym J 41:1097-1107 (Pubitemid 40305043)