Preparation of glucosaminyl muramic acid derivatives

Details Preparation of glucosaminyl muramic acid derivatives Preparation of glucosaminyl muramic acid derivatives

1995-10-04

1998-05-12

Peselev, Elli

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

Organic compounds

Carbohydrates or derivatives

536 185, C07H 500

Patent

active

057506655

ABSTRACT:
The present invention provides a method for the preparation of disaccharides, such as glucosaminyl muramic acids peptides and derivatives. The method includes condensing a protected muramic acid ester with a 1-organothio- or 1-fluoroglucosamine derivative in the presence of a suitable promoter to produce a protected glucosaminyl muramic acid ester. The protected glucosaminyl muramic acid ester may be used to prepare disaccharide peptides, such as N-acetylglucosaminyl-N-acetylmuramyl dipeptides, which have demonstrated immunological activity. Protected muramic acid esters and 1-organothio- or 1-fluoro- glucosamine compounds which may be employed as intermediates in the method are also provided.

REFERENCES:
patent: 4391800 (1983-07-01), Durette et al.
patent: 4395399 (1983-07-01), Ovchinnikov et al.
patent: 4545932 (1985-10-01), Takase et al.
patent: 4774231 (1988-09-01), Petitou et al.
patent: 4950645 (1990-08-01), Vosika et al.
patent: 5371022 (1994-12-01), Hasegawa
Kusumoto, et al., Bull. Chem. Soc. Jpn. 59, 1411-1417 (1986).
Termin, et al., Liebigs Ann. Chem. 527-533 (1992).
Baker, et al., J. Org. Chem., 19: 1786-1792, (Jun. 1954).
Bomford, et al., Aids Research and Human Retroviruses, 8: 1765-1771, (1992).
Durette, et al., Carbohydrate Research, 77: C1-C4, ( Aug. 1979).
Chapleur, et al., J. Chem. Soc. Perkin Trans., 1: 703-705, (1989).
Durette, et al., Tetrahedron Lett., 42: 4013-4016 (Apr. 1979).
Farkas, et al., Carbohydrate Research, 163: 63-72, (1987).
Flowers, et al., J. Org. Chem., 28: 2983-2986 (Nov. 1963).
Furuta, et al., Agric. Biol. Chem., 50 (10): 2561-2572 (Apr. 1986).
Gross, et al., Liebigs Ann. Chem., 37-45, (May 1986).
Guinand, et al., Eur. J. Biochem., 143: 359-362 (Feb. 1984).
Kanie, et al., J. Am. Chem. Soc., 116: 12073-12074 (Sep. 1994).
Kantoci, et al., Carbohydrate Research, 162: 227-235 (1987).
Kawata, et al., Agric. Biol. Chem., 48: 1783-1793 (1984).
Keglevic, et al., Biochimica et Biophysica Acta, 585: 273-281 (1979).
Keglevic, et al., Croatica Chemica Acta, 58: 569-581, (1985).
Kiso, et al., Carbohydrate Research, 104: 253-269 (Jan. 1982).
Kusumoto, et al., Bull. Chem. Soc. Jpn., 59:1419-1423 (Jan. 1986).
Kusumoto, et al., Tetrahedron Letters, 45: 4407-4410 (Aug. 1978).
Ledvina, et al., Collect. Czech. Chem. Commun., 54: 2784-2794 (Mar. 1989).
Ledvina, et al., Carbohydrate Research, 251: 269-284 (1994).
Merser, et al., Tetrahedron Letters, 13: 1029-1032 (1973).
Mukaiyama, et al., Chem. Lett., 431-432 (1981).
Nicolaou, et al., J. Am. Chem. Soc., 105: 2430-2434 (1983).
Nicolaou, et al., J. Am. Chem. Soc., 106: 4189-4192 (Mar. 1984).
Nicolaou, et al., J. Am. Chem. Soc., 107: 5556-5558 (Apr. 1985).
Nicolaou, et al., J. Am. Chem. Soc., 12: 3693-3695 (1990).
Pozsgay, et al., J. Org. Chem., 52: 4636-4637 (1987).
Pozsgay, et la., Tetrahedron Letters, 28, No. 13, 1375-1376 (Jan. 1987).
Pozsgay, et al., Carbohydrate Research, 179: 61-75 (1988).
Sava, et al., Cancer Immunol. Immunother, 15: 84-86 (1983).
Termin, et al., Liebigs Ann. Chem., 789-795 (1989).
Vosika, et al., J. of Immunotherapy, 10: 256-266 (Feb. 1991).
Campbell, et al. J. of Immunology, 145: 1029-1036 (Aug. 1990).

Affiliated with

Also associated with

Rating

Preparation of glucosaminyl muramic acid derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Preparation of glucosaminyl muramic acid derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Preparation of glucosaminyl muramic acid derivatives will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-980111