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, En outre, ils présentent une isomérie cis/trans des amides N,N-disubstitués. Mais cet inconvénient peut être rendu avantageux en utilisant des chaînes latérales spécifiques pour contrôler cette isomérie. En fonction des chaines latérales utilisées, les peptoïdes peuvent adopter des structures secondaires particulières comme des hélices. La structuration est basée principalement sur la conformation des amides N,N-disubstitués du squelette

I. Polyproline and . Ppi), Armand et Zuckermann ont démontrés par modélisation et RMN l'adoption d'une structure en hélice de type PPI d'un octamère portant des chaines volumineuses (S)-phényléthyle. 14 Plus tard

, De la même façon, lorsque les amides sont en trans, une structuration en hélice de type PolyProline 2 (PPII) est préférée. Par exemple, les oligomères de N-aryl glycines adoptent une structure hélicoïdale de type PPII homogène en solution, Cependant, la structure était hétérogène en solution avec la présence de conformères minoritaires

, Pour avoir une structure homogène de type PolyProline 1 (PPI), le groupe de Blackwell a développé des oligomères portant des chaines latérales naphtyléthyles. 16 Récemment, notre groupe a étudié des chaines latérales N-?-chirales mais en s'affranchissant de groupement aromatique présent dans les chaines actuellement utilisées

, Les études de RMN et dichroïsme circulaire ont montré une structuration en hélice de type

I. Polyproline and . Ppi)-d'une-grande-stabilité, confirmé par la structure cristallographique d'un pentamère de Ns1tbe. De plus, la construction d'oligomères mixtes comportant les chaines tBu et s1tbe a permis d'obtenir la structure RX du plus long oligomère reporté à ce jour

P. Armand,

K. L. Kirshenbaum;-a.-falicov;-r and . Dunbrack,

K. Dill,

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C. W. Wu,

K. J. Kirshenbaum;-t, ;. A. Sanborn, and . Patch,

K. Huang,

K. A. Dill;-r, ;. Zuckermann, and A. E. ,

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M. L. Huang,

M. A. Benson;-s, . J. Shin;-v, K. Torres;, and . Kirshenbaum, Amphiphilic Cyclic Peptoids That Exhibit Antimicrobial Activity by Disrupting Staphylococcus Aureus Membranes, European Journal of Organic Chemistry, pp.3560-3566, 2013.

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, Scheme 2Accès aux oligomères à base de 1,2,3-triazolium selon deux stratégies

, Enfin, la formation du triazolium a été étudiée sur support pour conduire aux oligomères amphiphiles cationiques. Sur la base de travaux antérieurs

, Nspe-Nspe)2-NH2 a été décroché du support et obtenu avec une bonne pureté évaluée par analyse LC-MS. En utilisant l'expérience acquise dans le groupe lors des travaux précédents sur la synthèse en solution d'oligomères à base de 1,2,3-triazolium et grâce à notre stratégie optimisée en phase solide développée ici

, Une étude préliminaire de dichroïsme circulaire de cette série d'oligomères a montré que les peptoïdes H-(Nchtm-Nspe-Nspe)2-NH2, H-(Nchtm + -Nspe-Nspe)2-NH2 et H

, Nspe)3-NH2 présentent la signature caractéristique de l'hélice de type PPI des peptoïdes portant des chaines spe avec deux minima à 203 et 220 nm. 33 L'intensité inférieure de l'hexapeptoïde H-(Nchtm-Nspe-Nspe)2-NH2 à base de triazole par rapport à l'hexapeptoïde à base de triazolium H-(Nchtm + -Nspe-Nspe)2-NH2 est révélatrice de la stabilisation de la structure hélicoïdale par les chaines de type triazolium. En outre, une signature CD similaire a été observée pour l'hexamère H-(Nchtm + -Nspe-Nspe)2-NH2

P. Armand,

K. A. Kirshenbaum;-r, ;. Goldsmith, and . Farr-jones,

A. E. Barron;-k and . Truong,

K. A. Dill;-d and . Mierke,

F. E. Cohen;-r, E. K. Zuckermann, and . Bradley, NMR Determination of the Major Solution Conformation of a Peptoid Pentamer with Chiral Side Chains, vol.95, pp.4309-4323, 1998.

. Nspe-nspe, 3-NH2, ce qui suggère que l'oligomère court a déjà une structure hélicoïdale bien définie et donc le caractère amphiphile nécessaire pour l'activité antibactérienne

, Chapitre IV Evaluation biologique

C. Dans-ce, L'évaluation biologique comprendra l'étude de l'activité antibactérienne, de l'activité hémolytique et de la viabilité cellulaire. Pour mieux comprendre le mode d'action de ces peptoïdes, nous décrirons l'évaluation biologique des différentes familles d'oligomères amphiphiles cationiques synthétisés précédemment