3,5-dioxa-12-azawurtzitane compound and process of preparing...

Details 3,5-dioxa-12-azawurtzitane compound and process of preparing... 3,5-dioxa-12-azawurtzitane compound and process of preparing...

2000-12-11

2002-05-07

Kifle, Bruck (Department: 1624)

Organic compounds -- part of the class 532-570 series

Organic compounds

Chalcogen in the nitrogen containing substituent

Reexamination Certificate

active

06384218

ABSTRACT:

BACKGROUND OF THE INVENTION
This invention relates to a 3,5-dioxa-12-azawurtzitane compound and a process of preparing same. The new class of dioxa-azawurtzitane compounds of the present invention have a structure similar to an amino acid or a polypeptide and will be utilizable for various applications, for example, as a molecular recognition agent for use in neurotransmission studies, an intermediate for a protein-resembling compound, a surfactant, a protective group and a host-guest complex for use as a sensor.
A dioxa-azawurtzitane of the following formula is reported by Hiroshi IZUMI and Shigeru FUTAMURA in J. Chem. Soc., Perkin Trans. 1, 1925 (1998):
in which Me stands for a methyl group and R stands for a 4-methoxybenzyl group, a 2-(pyridin-2-yl)ethyl group or a 2-(imidazol-4-yl)ethyl group. The known wurtzitane compounds do not have a structure similar to an amino acid or a polypeptide.
SUMMARY OF THE INVENTION
It is an object of the present invention to provide a 3,5-dioxa-12-azawurtzitane compound having a structure similar to an amino acid or a polypeptide.
In accordance with one aspect of the present invention, there is provided a 3,5-dioxa-12-azawurtzitane compound represented by the following formula (I):
wherein R
1
represents an alkyl group, R
2
represents a group which, together with a —CH(NH
2
)COOH group, constitutes an &agr;-amino acid of the formula R
2
CH(NH
2
)COOH and which may contain one or more substituents and R
3
represents a hydroxyl group or a group obtained by removing a hydrogen atom of the terminal amino group of an oligo- or polypeptide or a polyamino acid.
In another aspect, the present invention provides a process of preparing a 3,5-dioxa-12-azawurtzitane compound represented by the following formula (I):
wherein R
1
represents an alkyl group, R
2
represents a group which, together with a —CH(NH
2
)COOH group, constitutes an &agr;-amino acid of the formula R
2
CH(NH
2
)COOH and which may contain one or more substituents and R
3
represents a hydroxyl group or a group obtained by removing a hydrogen atom of the terminal amino group of an oligo- or polypeptide or a polyamino acid, said process comprising reacting an amino acid, an oligo- or polypeptide or a polyamino acid with a trialdehyde represented by the following formula (II):
wherein R
1
has the same meaning as above.
In the present specification and claims, the three R
1
s bonded to the carbon atoms at 1-, 7- and 9-positions of the 3,5-dioxa-12-azawurtzitane compound of the formula (I) or at 1-, 3- and 5-positions of the trialdehyde of the formula (II) may be the same or different alkyl groups.
Other objects, features and advantages of the present invention will be apparent from the detailed description of the preferred embodiments of the invention to follow.


REFERENCES:
J. Org. Chem, 1999, 64, 4502-4505, Izumi et al.
J. Chem. Soc., Perkin Trans. 1, 1998, 1925-1928, Izumi et al.
Journal of the Chemical Society, Col. 1, 1998, pp. 1925-1928.
Journal of Organic Chemistry, American Chemical Society, vol. 64, 1999, pp. 4502-4505.
J. Org. Chem., vo. 62, 1997, pp. 1173-1175.
Chem. Commun., 1996, pp. 27-28.
Chemistry Letters, No. 9, 1985, Vpp. 759-760.

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