Synthesis and polymerization of conveniently substituted 6-amino-6-deoxy-D-galactonic acid derivatives
Methyl 6-azido-6-deoxy-2,3:4,5-di-O-isopropylidene-D-galactonate (1), prepared in two steps from D-galactono-1,4-lactone, was hydrolyzed to the corresponding acid 2, which was esterified with phenol (PhOH) in the presence of dicyclohexylcarbodiimide (DCC) to give the phenyl ester 3. Hydrogenolysis o...
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todo:paper_14246376_v2005_n12_p76_RomeroZaliz2023-10-03T16:13:43Z Synthesis and polymerization of conveniently substituted 6-amino-6-deoxy-D-galactonic acid derivatives Romero Zaliz, C.L. Erra-Balsells, R. Nonami, H. Sato, Y. Varela, O. Acetal D-galactonic acid Polyamide Polymerization Sugar amino acids Methyl 6-azido-6-deoxy-2,3:4,5-di-O-isopropylidene-D-galactonate (1), prepared in two steps from D-galactono-1,4-lactone, was hydrolyzed to the corresponding acid 2, which was esterified with phenol (PhOH) in the presence of dicyclohexylcarbodiimide (DCC) to give the phenyl ester 3. Hydrogenolysis of the azide function of 3 yielded the hydrochloride derivative of the amino acid 4. Compound 4 is conveniently substituted for the polycondensation; therefore, this reaction was conducted using DMF as solvent and N,N-diisopropylethylamine as a basic catalyst. The MALDI-TOF mass spectrum of the isolated product (5) indicated that this was a mixture of the cyclic trimer (M + Na+, 793.7) and linear oligomers (from the tetramer to the tetradecamer). To favor the linear polymerization the dimeric amino acid 10 was prepared starting from 2. Thus, hydrogenation of 2 gave the amino acid 6, and treatment of 2 with pentachlorophenol-DCC gave the pentachlorophenyl ester 7. Coupling of 6 with 7 in the presence of DCC gave the dimer 8, which was converted (PhOH, DCC) into 9. Hydrogenolysis of 9 afforded the dimeric amino acid 10, which was polymerized under the conditions employed for 4. The resulting polyamide 11 was highly soluble in common organic solvents, and its molecular weight was established by MALDI-TOF MS and size exclusion chromatography (Mw = 2700). ©ARKAT. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p76_RomeroZaliz |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Acetal D-galactonic acid Polyamide Polymerization Sugar amino acids |
| spellingShingle |
Acetal D-galactonic acid Polyamide Polymerization Sugar amino acids Romero Zaliz, C.L. Erra-Balsells, R. Nonami, H. Sato, Y. Varela, O. Synthesis and polymerization of conveniently substituted 6-amino-6-deoxy-D-galactonic acid derivatives |
| topic_facet |
Acetal D-galactonic acid Polyamide Polymerization Sugar amino acids |
| description |
Methyl 6-azido-6-deoxy-2,3:4,5-di-O-isopropylidene-D-galactonate (1), prepared in two steps from D-galactono-1,4-lactone, was hydrolyzed to the corresponding acid 2, which was esterified with phenol (PhOH) in the presence of dicyclohexylcarbodiimide (DCC) to give the phenyl ester 3. Hydrogenolysis of the azide function of 3 yielded the hydrochloride derivative of the amino acid 4. Compound 4 is conveniently substituted for the polycondensation; therefore, this reaction was conducted using DMF as solvent and N,N-diisopropylethylamine as a basic catalyst. The MALDI-TOF mass spectrum of the isolated product (5) indicated that this was a mixture of the cyclic trimer (M + Na+, 793.7) and linear oligomers (from the tetramer to the tetradecamer). To favor the linear polymerization the dimeric amino acid 10 was prepared starting from 2. Thus, hydrogenation of 2 gave the amino acid 6, and treatment of 2 with pentachlorophenol-DCC gave the pentachlorophenyl ester 7. Coupling of 6 with 7 in the presence of DCC gave the dimer 8, which was converted (PhOH, DCC) into 9. Hydrogenolysis of 9 afforded the dimeric amino acid 10, which was polymerized under the conditions employed for 4. The resulting polyamide 11 was highly soluble in common organic solvents, and its molecular weight was established by MALDI-TOF MS and size exclusion chromatography (Mw = 2700). ©ARKAT. |
| format |
JOUR |
| author |
Romero Zaliz, C.L. Erra-Balsells, R. Nonami, H. Sato, Y. Varela, O. |
| author_facet |
Romero Zaliz, C.L. Erra-Balsells, R. Nonami, H. Sato, Y. Varela, O. |
| author_sort |
Romero Zaliz, C.L. |
| title |
Synthesis and polymerization of conveniently substituted 6-amino-6-deoxy-D-galactonic acid derivatives |
| title_short |
Synthesis and polymerization of conveniently substituted 6-amino-6-deoxy-D-galactonic acid derivatives |
| title_full |
Synthesis and polymerization of conveniently substituted 6-amino-6-deoxy-D-galactonic acid derivatives |
| title_fullStr |
Synthesis and polymerization of conveniently substituted 6-amino-6-deoxy-D-galactonic acid derivatives |
| title_full_unstemmed |
Synthesis and polymerization of conveniently substituted 6-amino-6-deoxy-D-galactonic acid derivatives |
| title_sort |
synthesis and polymerization of conveniently substituted 6-amino-6-deoxy-d-galactonic acid derivatives |
| url |
http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p76_RomeroZaliz |
| work_keys_str_mv |
AT romerozalizcl synthesisandpolymerizationofconvenientlysubstituted6amino6deoxydgalactonicacidderivatives AT errabalsellsr synthesisandpolymerizationofconvenientlysubstituted6amino6deoxydgalactonicacidderivatives AT nonamih synthesisandpolymerizationofconvenientlysubstituted6amino6deoxydgalactonicacidderivatives AT satoy synthesisandpolymerizationofconvenientlysubstituted6amino6deoxydgalactonicacidderivatives AT varelao synthesisandpolymerizationofconvenientlysubstituted6amino6deoxydgalactonicacidderivatives |
| _version_ |
1782030295582638080 |