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Abstrak :
ABSTRAK Telah dilakukan sintesis senyawa 3-hidroksi pikolinil serin oktil ester (PSOE) dan turunannya melalui 3 tahap reaksi, yaitu sintesis senyawa oktil serin ester p-TsOH, sintesis senyawa PSOE dan sintesis senyawa PSOAE, PSOHE, PSOOE, PSOPPE. Sintesis senyawa oktil serin ester p-TsOH memberikan hasil 69,9 %. Sintesis senyawa PSOE memberikan hasil 29,7 %, sedangkan sintesis senyawa PSOAE, PSOHE, PSOOE dan PSOPPE berturut-turut memberikan hasil 31,8 %, 67,7 %, 40 % dan 46,17 %. Hasil uji aktifitas antibiotika terhadap mikroba E. coil, S. aureus, B. subtilis dan C. albicans menunjukkan bahwa senyawa hasil sintesis memberikan aktifitas anti bakteri paling baik terhadap B. subtilis dan aktifitas anti jamurnya lemah terhadap C. albicans. Hasil uji brine shrimp Artemia salina (BSLT) menunjukkan efek toksisitas senyawa PSOOE > PSOHE > PSOAE > PSOE > PSOPPE.

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ABSTRACT The Syntheses and Bioassay of Novel Antibiotics 3-Hidroxy Pycolinyl Serine Octyl Ester and its DerivativesThe 3-hidroxy pycolinyl serine octyl ester (PSOE) and its derivatives i.e. PSOAE, PSOHE, PSOOE and PSOPPE have been synthesized. These compounds were synthesized in three step reactions. The first step produced serine octyl ester p-TsOH in 69,9 %. The second step resulted PSOE in 29,7 %. The last step produced PSOAE, PSOHE, PSOOE and PSOPPE in 31,8 %, 67,7 %, 40,0 % and 46,17 % respectively. The biological assay of these compounds showed activity against E. coil, S. aureus, B. subtilis and C. albicans, in which the activity against B. subtilis was the strongest. In fact the activity of these compounds were stronger than that of standard antimycin A. The activity of these compounds showed no activity against fungus C. albicans. The Brine Shrimp Lethality Test (BSLT) by using Artemia salina was performed to show toxicity of these compounds. The toxicity was PSOOE > PSOHE > PSOAE > PSOE > PSOPPE.

Abstrak :
Senyawa antibiotika memegang peranan penting di dalam pengobatan berbagai macam penyakit infeksi baik yang disebabkan oleh mikroba maupun yang disebabkah oleh virus. Senyawa - antibiotika UK-3 telah diisolasi dari miselium Streptomyces-sp. 517-02 -dan diketahui mempunyai aktivitas dalam menghambat pertumbuhan bakteri dan sel kanker. Total sintesis senyawa UK-3 dan analognya juga telah dilakukan. Penelitian ini bertujuan untuk mensmtesis senyawa Analog UK-3 (SH-I, SH-3) yang diharapkan mempunyai aktivitas yang lebih besar dari senyawa aslinya. Metode sintesis yang digunakan adalah melalui tiga tahap reaksi. Tahap pertama adalah reaksi esterifika L-seiin dan heksanol dengan katalis asam p-TsOH dalam bonzen. Selanjutnya pada tahap kedua adalah pembentukan 2-hidroksinikotinil-heksil-serin-ester antara asam 2-hidroksinikotinat dan heksilserin-ester-p-TsOH dengan katalis/aktivator DMAP/DCC dalam piridin. Reaksi terakhir adalah esterifikasi senyawa 2-hidroksinikotinil-serin-heksil-ester dengan anhidrida asetat dalam piridin menghasilkan SH-l, dengan asam fenil propanoat dan oktanoat dengan DMAP/DCC dalamdiklorometan masing-masing menghasilkan SH-2 dan SH-3. Senyawa hasil sintesis diidentifikasi dengan menggunakan spektrofotometer Infra Merah (FT-IR), spektrometer Resonansi Magnetik-Inti (1H-NMR), spektrofotometer, Ultra Violet dan -spektrometer- Massa (MS). Pengujian aktivitas senyawa analog UK-3 dilakukan dengan uji antimikroba-terhadap beberapa mikroba dan uji toksisitas terhadap Brine Shrimp. Senyawa SH-3 aktif menghambat pertumbuhan terhadap bakteri Escherichia coil dan Candida albicans sampai konsentrasi 75 ppm, sedang SH-2 menunjukkan aktivitas paling tinggi terhadap uji Brine Shrimp dengan nilai LC50 pada konsentrasi 700,22 ppm.

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The Synthesis And Biological Activity Test Of Antibiotic UK-3 Analogues (2-idroxynicotinyl-Hexyl-Serine-Ester-And Its Derivatives) Antibiotic compounds play important role in medical treatment of various infection diseases either caused by microbes or viruses. The Antibiotic UK-3 has been isolated from mycelim Streptomyces sp. 517-02 and found that its activity inhibits the growth of bacteria and cancer cells. Total synthesis of UK-3 and its analogues have been conducted as well. The goal of this research is to synthesize various analogues of UK-3 (SH-1, SH-2, SH-3) which is hoped to have higher activities than that of the original compound. The synthesis method consist of three reaction steps. The first step is esterification reaction of -L-serine and hexanol with catalyst p-TsOH in -benzene. The -second -step is the formation of -2-hydroxynicotinyl-hexyl-serine-ester between 2-hydroxynicotinyl acid and hexyl-serine-ester with catalyst/activator DMAPIDCC in pyridine. The last reaction is esterification of 2 hydroxynicotinyl-serine-ester-compound and acetic-anhydrid in pyridine - which form SH-1. If phenyl propionic acid or octanoic acid was used in the presence of DCCIDMAP in dichloromethane, the product formed was SH-2 and SH-3. The product of each step was identified and characterized by means Infra Red spectrophotometer (FTIR), 1H-NMR spectrometer, UV spectrophotometer and Mass spectrometer. The activity of SH-l, SH-2 and SH-3 as antimicrobes tested against several microorganism and their toxicity was tested against Brine Shrimp. SH-3 was found active against E. coil and C. albicans up to the concentrations of 75 ppm, while SH-2 indicated the highest activity on Brine Shrimp test with the value of LC50 in the concentrations of 700,22 ppm.