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Synthesis, CD Spectra, and Enzymatic Stability of??2-Oligoazapeptides Prepared from (S)-2-Hydrazino Carboxylic Acids Carrying the Side Chains of Val, Ala, and Leu, Helvetica Chimica Acta, vol.86, issue.12, pp.4152-4258, 1998. ,
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C=O) 3444 (=CH) RMN 1 H (CDCl 3 , 400 MHz) : ? (ppm) : 1,41 (s, 3H, pp.1745507125-380 ,
23 mmol) est dissout dans 5 mL de tétrahydrofurane. La solution est portée à 0°C puis 4 éq mL, 0,92 mmol) sont additionnés. Le mélange est agité pendant 4 heures à température ambiante. Le mélange est ensuite refroidi à 0°C et 14 mL de soude (2M) sont additionnées suivi de 9,5 mL de peroxyde d'hydrogène. L'agitation est maintenue une heure, le mélange réactionnel est ensuite lavé par 20 mL d'eau, la phase organique est séchée sur MgSO 4 , concentrée sous pression réduite. Le résidu est purifié par chromatographie sur gel de silice avec le mélange éluant H, mmol) est obtenu avec un rendement de 61 %, sous la forme d'un mélange de diastéréoisomères inséparables, p.2109514 ,
98 (m, 4H, 4x-OCH 2 Ph, pp.80-416 ,
40 (dd, 1H, J gem = 16,1 Hz, J 2'a-3' = 8,3 Hz (dd, 1H, J 2'b-3' = 4,3 Hz, RMN 1 H (CDCl 3 , 250 MHz) : ? (ppm) : 2, pp.5643-3699341 ,
BOP 2 avec 350 mg d'amine 222 (0,5 mmol), 129 mg d'acide aminé 217 (0,625 mmol), 357 mg de Py-BOP (0,625 mmol) et 96 µL de triéthylamine (0,625 mmol) Le brut est purifié sur colonne chromatographique avec le mélange éluant H, p.75 ,
400 MHz) : ? (ppm) : 1,47 (s, 9H, Hz, J 2'a-3' = 2,8 Hz, J 2'b-3' = 2,4 Hz 2 PhNH (amide) ), pp.1739-1745 ,
Analyse : Calculée : C : 72,12 H : 7,38 N : 4,10, Trouvée : C : 71,92 H : 7,19 N : 4,10. RMN 1 H (CDCl 3 , 400 MHz) : ? (ppm) : 1,43 (s, 9H, 2 Ph, pp.1700-1703 ,
,8-tétra-O-benzyl-D-glycero-D-ido-octitol-1-yl]-2-[tert- butyloxyacetyl]-(tert-butoxycarbonyl) hydrazine 251, 2006. ,
,8-tétra-O-benzyl]-1-[(tert-butyloxyacetyl)amino]- 1, p.256, 2006. ,
19 mmol) est mis en solution dans 5 mL d'un mélange acétonitrile/diéthylamine (2/1 en volume) Au bout d'une heure d'agitation à température ambiante, le milieu réactionnel est concentré sous pression réduite. Le brut réactionnel est purifié par chromatographie sur gel de silice avec un mélange éluant H/AE : 3/1, p.248 ,
C=O) 3428 (NH) RMN 1 H (CDCl 3 , 250 MHz) : ? (ppm) : 1,43 (s, 9H, 3xCH 3(tBu) ), 1,50 (s, 3H, CH 3, 2 Ph), pp.172860-124, 1921. ,
Ala-OtBu 264 (65 mg, 1,1 éq., 0,45 mmol) suivant la méthode générale de couplage 11 en utilisant 1,5 éq. de NMM (52 µL, 0,60 mmol) et 1,5 éq. d'ICF (90 µL, 0,60 mmol) Après une purification par chromatographie moyenne pression sur gel de silice avec le mélange éluant H/AE : 1/3, pp.25-265 ,
(s, 1H, pp.411533-411540 ,
(s, 2H, -OCH 2 Ph, pp.99-40705 ,
45 mmol) sont alkylés en présence de 1,3 éq. de bromoacétate de tert-butyle (0,1 mL, 0,58 mmol) et de 43 mg de K 2 CO 3 (1 éq., 0,45 mmol) Après une purification par chromatographie moyenne pression sur gel de silice avec le gradient d'éluant H/AE : 3/2 à AE pur, pp.270-272 ,
mmol) est mis en solution dans 10 mL d'un mélange acide trifluoroacétique-méthanol (1/1 en volume) Le milieu est maintenu sous agitation pendant 18 heures puis il est concentré sous pression réduite, Le brut réactionnel est utilisé sans autre purification, p.15 ,