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___________________________________________________RESULTADOS E DISCUSSÃOAB14'13'12'11'10'9'8'7'6'5'4'3'2'O1'NH4 531O2HOH-2’ d, 5,83 ppm; 15,3 HzH-3’, dt; 6,92 ppm; 15,3 e6,9 HzFigura 36. A. Espectro de RMN de 1 H (499,88 MHz, CDCl 3 , TMS) da fraçãoF22 proveniente do cultivo de M. mesophilicum. B. Ampliação da região entre5,0-7,0 ppm.71
___________________________________________________RESULTADOS E DISCUSSÃOEm aproximadamente 6,92 ppm, pode-se observar os sinais relativos aohidrogênio H-3’ da porção da (S)-N-(2E,7Z)-tetradecadienil-HSL, que é a acil-HSL mais abundante da amostra (Figura 32B). A constante de acoplamento deJ=15,3 Hz também foi observada no sinal do hidrogênio H-2’ (5,83 ppm)denotando claramente a geometria trans para a insaturação presente naposição 2 da cadeia acila lateral.Tanto a (S)-N-(2E,7Z)-tetradecadienil-HSL quanto a (S)-N-(7Z)-tetradecenoil-HSL possuíam uma insaturação na posição 7 da cadeia acilalateral. Como pode ser observado na Figura 35, ambas substâncias estãopresentes em proporções semelhantes na amostra, e os sinais dos hidrogêniosH-7’ e H-8’ se sobrepuseram no espectro de RMN de 1 H (Figura 36A).Entretanto, recentemente Penalver e colaboradores (2006) reportaram oisolamento destes metabólitos produzidos por Methylobacterium extorquens,uma espécie extremamente próxima de M. mesophilicum, objeto do presenteestudo. Em seu artigo, Penalver reportou os espectros de RMN de 1 H destesmetabólitos, e a comparação com os dados espectrais mostrou que ambasmoléculas no presente estudo possuem a insaturação na posição 7 comgeometria cis com (Figura 37). Outras comparações espectrais foram possíveisapós o isolamento da (S)-(7Z)-tetradecenoil-HSL dos caldos de cultivo de M.mesophilicum, detalhado no tópico 3.3.3.1, em meio TSB.72
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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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PARTE EXPERIMENTAL5. PARTE EXPERIME
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PARTE EXPERIMENTAL• Espectroscopi
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PARTE EXPERIMENTAL5.1.2. Meios de c
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PARTE EXPERIMENTAL5.1.4. Cepas bact
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PARTE EXPERIMENTAL(S)-N-heptanoil-h
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PARTE EXPERIMENTAL(R)-(+)-N-heptano
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PARTE EXPERIMENTAL5.3. Avaliação
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PARTE EXPERIMENTALhexano, diclorome
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PARTE EXPERIMENTAL4,47 (t, 1H, J 9,
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PARTE EXPERIMENTAL13' 11' 9' 7' 5'O
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PARTE EXPERIMENTALHinton contendo o
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PARTE EXPERIMENTALno caso dos meios
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PARTE EXPERIMENTAL(S)-N-tetradecano
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PARTE EXPERIMENTALAs acil-HSLs fora
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PARTE EXPERIMENTAL5% (2 x 6 mL), bi
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PARTE EXPERIMENTAL13'12'11'10'9'8'7
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PARTE EXPERIMENTALsinais sobreposto
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PARTE EXPERIMENTALóleo e ferveu-se
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PARTE EXPERIMENTALRMN de 13 C (75,4
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PARTE EXPERIMENTAL(S)-(2E)-N-dodece
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PARTE EXPERIMENTAL(S)-3-oxo-(7Z)-N-
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PARTE EXPERIMENTAL5.4.9.3. Obtenç
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PARTE EXPERIMENTALIV (KBr): 3318, 3
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PARTE EXPERIMENTALisotermicamente a
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PARTE EXPERIMENTALprocedimento, por
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REFERÊNCIAS BIBLIOGRÁFICAS6. REFE
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REFERÊNCIAS BIBLIOGRÁFICASClusia
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REFERÊNCIAS BIBLIOGRÁFICASENGEBRE
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REFERÊNCIAS BIBLIOGRÁFICASLAMBAIS
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REFERÊNCIAS BIBLIOGRÁFICASusing l
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REFERÊNCIAS BIBLIOGRÁFICASXylella
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