Синтез циклических ?-(1>6) — связанных олигосахаридов и олигодентатных конъюгатов на их основе

6. выводы.

1. Впервые осуществлён синтез индивидуальных представителей нового класса циклических олигосахаридов — олиго-р-(1 —>6)-0-глюкозаминов, содержащих от двух до семи остатков D-глюкозамина.

2. Установлено, что циклизация линейных бифункциональных олигосахаридов, состоящих из 4−7 остатков D-глюкозамина, приводит к образованию побочных циклических продуктов с а-гликозидной связью, несмотря на наличие соучаствующей фталимидной группы в положении 2 гликозилирующего остатка. Предложено объяснение этого необычного факта, основанное на конформационных особенностях линейных олиго-?-(1—>6)-0-глюкозаминов.

3. Исследования зависимости стереохимии реакции циклогликозилирования от структурных факторов и условий проведения реакции, проведённые на примере циклизации различных ß—(l—>6)-связанных тетрасахаридов, показали, что основным фактором, определяющим стереохимический результат циклизации, является заместитель во втором положении гликозилирующего остатка.

4. Продемонстрирована возможность применения циклоолигоглюкозаминов в качестве носителей для синтеза олигодентатных конъюгатов: получена серия из 15 гл и ко кластеров на основе циклических ди-, трии тетрасахаридов, к аминогруппам которых посредством спейсеров различной природы и длины присоединены остатки D-галактозы.

5. С помощью различных методов (HIA, ELLA, ITC) определена аффинность синтезированных гликоконъюгатов к белку LecA. Показано, что степень связывания кластеров с лектином возрастает с увеличением количества D-галактозных лигандов и степени жесткости линкеров. Найден наиболее эффективный блокатор LecA из известных на данный момент.

6. Получена серия из 15 гликоконъюгатов, состоящих из циклоолигосахаридных матриц и гидрофобных цепей различной длины, которые являются перспективными агентами для создания ионных каналов в клеточных мембранах.

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