PARTE EXPERIMENTAL14'13'12'11'10'9'8'7'6'5'4'O3'2'O1'NH4 53 1 2OO(±)-N-(3-oxo-tetra<strong>de</strong>canoil)-homosserina lactona. Rendimento global:46,8 %. R f 0,526 (AcEt 100%). CG-EM (IE, 70 eV) <strong>de</strong>composição.IV (KBr). 3298, 2920, 2850, 1772, 1716, 1641, 1549, 1178, 1015, 721cm -1 .RMN <strong>de</strong> 1 H (300,06 MHz, CDCl 3 , TMS): δ 0,88 (t, 3H, J 6,7 Hz, H-14’); 1,26 (m, 16H, H-13’, H-12’, H-11’, H-10’, H-9’, H-8’, H-7’, H-6’);1,58 (quinteto, 2H, J 7,0 Hz, H-5’); 2,25 (m, 1H, H-4); 2,53 (t, 2H, J 7,3 Hz,H-4’); 2,74 (m, 1H, H-4); 3,47 (s, 2H, H-2’); 4,27 (ddd, 1H, J 11,0; 9,2 e 6,1Hz, H-5); 4,48 (t, 1H, J 9,2 Hz, H-5); 4,62 (ddd, 1H, J 11,0; 8,9 e 7,0 Hz, H-3); 7,73 (d, NH, J 6,4 Hz).RMN <strong>de</strong> 13C (75,45 MHz, CDCl3, TMS): δ 14,1 (C-14’); 22,7 (C-13’); 23,4 (C-12’); 29,0 (C-11’); 29,3 (C-9’); 29,4 (C-8’); 29,4 (C-7’); 29,6(C6’, C5’); 29,7 (C-4); 31,87 (C-10’); 43,9 (C-4’); 48,2 (C-2’); 49,0 (C-3);65,9 (C-5); 166,5 (C-1’); 175,0 (C-2); 206,6 (C-3’).13' 11' 9' 7' 5'O O3'14' 12' 10' 8' 6' 4' 2'1'NH4 53 1 2HO(S)-N-(3-oxo-tetra<strong>de</strong>canoil)-homosserina lactona. Rendimento global: 54,0%. Os da<strong>do</strong>s <strong>de</strong> CG-EM, RMN <strong>de</strong> 1 H e 13 C são idênticos aos obti<strong>do</strong>s para a(±)-N-(3-oxo-tetra<strong>de</strong>canoil)-HSL. [α] 20 D –14º (c. 0,50 MeOH).O145
PARTE EXPERIMENTAL13' 11' 9' 7' 5'O O3'14' 12' 10' 8' 6' 4' 2'1'NH4 5 13 2HO(R)-N-(3-oxo-tetra<strong>de</strong>canoil)-homosserina lactona. Rendimento global: 50,7%. Os da<strong>do</strong>s <strong>de</strong> CG-EM, RMN <strong>de</strong> 1 H e 13 C são idênticos aos obti<strong>do</strong>s para a(±)-N-(3-oxo-tetra<strong>de</strong>canoil)-HSL. [α] 20 D +11º (c. 0,50 MeOH).O5.3.2. Bioensaios <strong>de</strong> ativida<strong>de</strong> antimicrobiana contra bactérias Grampositivas.5.3.2.1. Ensaio semi-quantitativo preliminar – análise visualOs ensaios antimicrobianos foram feitos com as bactérias GrampositivasStaphylococcus aureus CCT 1295, Bacilus cereus CCT 4060 eBacilus subtillis CCT 0089.Os inóculos <strong>do</strong>s microrganismos foram prepara<strong>do</strong>s em slants conten<strong>do</strong>meio cal<strong>do</strong> nutriente sóli<strong>do</strong> (3 tubos cada), cresci<strong>do</strong>s a 30 ºC por 24 horasem BOD. Após crescimento, as células foram removidas com alça flambadae suspendidas em água <strong>de</strong>stilada estéril (10 mL), até obter uma suspensãocom turbi<strong>de</strong>z equivalente a 3 x 10 8 ufc/mL, <strong>de</strong> acor<strong>do</strong> com uma escala <strong>de</strong>McFarland. No caso <strong>do</strong>s ensaios preliminares, foram toma<strong>do</strong>s 5 mL <strong>de</strong>stasuspensão e adiciona<strong>do</strong>s em 50 mL <strong>de</strong> meio Miller-Hinton, que foi emseguida pipeta<strong>do</strong> (100 μL) para a microplaca <strong>de</strong> 96 poços (as placas forampreviamente lavadas com água em abundância, sêcas e esterilizadas porexposição à lâmpada UV durante 1 hora). No topo <strong>de</strong> cada coluna (emduplicata), foram pipeta<strong>do</strong>s 100 μL <strong>de</strong> cada solução a ser testada (branco,146
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VDEDICATÓRIADEDICO ESTE TRABALHO
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VIIIBraga, Dr. José Augusto R. Rod
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XPOMINI, A. M. ; CABEÇA, L. F. ; C
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XIIde cadeia longa. Realizou-se tam
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XIVacyl-HSLs. We have also studied
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XVINBNOEODPpmR fRMNROERLUSTDSAMTMST
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XVIII3.3.4.2. Síntese da (S)-N-(2E
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XX5.4.10. Co-injeções das acil-HS
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