PREPARASI DAN MODIFIKASI KIMIA STRUKTUR KITOOLIGOSAKARIDA-2,5-ANHIDRO-D-MANNOFURANOSA (KOSAMF) DARI KITOSAN SERTA UJI ANTIBAKTERI TERHADAP Staphylococcus aureus DAN Escherichia coli
Keywords:kitosan, kitooligosakarida-2, 5-anhidro-D-mannofuranosa, aminasi reduktif, antibakteri
Kitooligosakarida-2,5-anhidro-D-mannofuranosa (KOSamf) dipersiapkan dengan derajat polimerisasi tertentu melalui reaksi nitrous deaminasi dari kitosan parsial N-deasetilasi. KOSamf kemudian diubah menjadi turunan KOSamf dengan mengkopling gugus aldehid yang terdapat pada unit 2,5-anhidro-D-mannofuranosa (amf). KOSamf dengan 3,5-dikloroanilin dan NaBH3CN dalam pelarut buffer ammonium asetat direaksikan melalui metoda one-pot aminasi reduktif untuk menghasilkan turunan KOSamf yang berpotensi sebagai senyawa antibakteri dan antijamur. Struktur kimia dari turunan KOSamf yang telah disintesis dikarakterisasi dengan Spektroskopi FT-IR dan NMR. Senyawa turunan KOSamf memiliki aktivitas sebagai antibakteri terhadap bakteri Staphylococcus aureus dengan zona inhibisi 12,5 mm dan bakteri E. coli dengan zona inhibisi 10,5 mm.
Chitooligosaccharide with a 2,5-anhydro-D-mannofuranose unit at the reducing end (COSamf) was prepared in certain degree of polymerization by nitrous deamination of a partial N-deacetylated chitosan. COSamf was then modified into COSamf derivative by functionalizing its 2,5-anhydro-D-mannofuranose (amf) unit. Therefore, one-pot reductive amination of COSamf in ammonium acetate buffer by 2,5-dichloroaniline and NaBH3CN was applied. This route was effective to generate antibacterial COSamf derivative in high yield. The structure of synthesized COSamf derivative was characterized by FT-IR and NMR spectroscopies. COSamf derivative has antibacterial activity against Staphylococcus aureus and Escherichia coli with diameter zone of inhibition 12.5 mm and 10.5 mm, respectively.
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