Building Units of Oligosaccharides, IC. – Preparation of Synthetic Antigens of the Inner Core Region of Lipopolysaccharides by Copolymerisation with Acrylamide
Besides L‐α‐D‐Hepp‐OAll (5), the following allyl glycosides with oligosaccharide structures of the inner core region of lipopolysaccharides have been synthesized: L‐α‐D‐Hepp‐(1→7)‐L‐α‐D‐Hepp‐OAll (19), L‐α‐D‐Hepp‐(1→3)‐L‐α‐D‐Hepp‐OAll (26), L‐α‐D‐Hepp‐(1→5)‐α‐Kdop‐OAll (31), L‐α‐D‐Hepp‐(1→5)‐β‐Kdop‐OAll (34), L‐α‐D‐Hepp‐(1→5)‐[α‐Kdop‐(2→4)]‐α‐Kdop‐OAll (48) and L‐α‐D‐Hepp‐(1→5)‐[α‐Kdop‐(2→4)]‐β‐Kdop‐OAll (39). All these compounds have been coupled with cysteamine to the spacer‐elongated derivatives 54b – 60b and finally converted into the acryloyl compounds 54c – 60c. The copolymerisation of 54c – 60c with acrylamide gave the polymers 54d – 60d, containing the above mentioned oligosaccharides as haptens in an antigenic form.
Bei gramnegativen Bakterien sind in der Regel Lipopolysaccharide (LPS) in der aul3eren Membran der Bakterien fixiert, die fur deren Serotyp spezifisch und deren immunologischen Eigenschaften verantwortlich sind. Von den LPS ist der Lipoid A-Teil mit seinen Fettsauren zur Fixierung in die' Doppelschicht der Membran integriert. Das Lipoid A ist uber die innere Core-Region mit den O-spezifischen Ketten verknupft. Die 0-spezifischen Ketten variieren stark in ihrer Struktur, wahrend fur die Core-Struktur ein weitgehend einheitliches Strukturschema gefunden wird. Hierbei wird in der Regel die Heptoseregion uber die KDO (3-Desoxy-~-rnanno-2-octulosonsaure)-Region verknupft *).
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