Process for preparing lipid II

Details Process for preparing lipid II Process for preparing lipid II

2007-01-30

2007-01-30

Lewis, Patrick (Department: 1623)

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

Organic compounds

Carbohydrates or derivatives

C536S055300, C536S123100, C536S123130, C536S124000, C536S127000

Reexamination Certificate

active

09833647

ABSTRACT:
A process is described for preparing a substrate for the transglycosylase enzymes of bacterial cell wall biosynthesis. The chemical synthesis makes available a sustainable and substantially pure source of supply of lipid II, including analogs thereof, that may be used in the identification of new therapeutic agents capable of disrupting steps in bacterial cell wall biosynthesis.

REFERENCES:
patent: 4395399 (1983-07-01), Ovchinnikov et al.
patent: 5141674 (1992-08-01), Leigh
patent: 5506204 (1996-04-01), Aston
Van Heijenoort et al. Journal of Bacteriology (1992), vol. 174, pp. 3549-3557.
Ye et al. J. Am. Chem. Soc. (2001), vol. 123, pp. 3155-3156.
Schwartz et al. J. Am. Chem. Soc. (2001), vol. 123, pp. 11638-11643.
C. Merser, et al., “Synthesis of the Repeating Disaccharide Unit of the Glycan Moiety of the Bacterial Cell Wall Peptidoglycan”′Tetrahedron Lett., No. 13, pp. 1029-1032 (1973).
P.L. Durette, et al., “Synthesis ofO-(2-acetamido-2-deoxy-β-D-glucosyl)—(1→4)-N-acetylmuramoyl-L-alanyl-D-isoglutamine, the repeating disaccharide-dipeptide unit of the bacterial cell-wall peptidoglycan”,Carbohydr. Res., vol. 77 pp. C1-C4 (1979).
S. Kusumoto, et al., “Chemical Synthesis and Biological Activities of Two Disaccharide Dipeptides Corresponding to the Repeating Units of Bacterial Peptidoglycan”,Bull. Chem. Soc. Jpn., vol. 59, pp. 1411-1417 (1986).
S. Kusumoto, et al., “Synthesis of β(1-4)—Linked Disaccharides ofN-Acetylglucosamine andN-Acetylmuramic Acid by Their Direct Condensation”Bull. Chem. Soc. Jpn., vol. 59, pp. 1419-1423 (1986).
J. Farkas, et al., “The Synthesis ofO-(2-Acetamido-2-Deoxy-β-D-Glucopyranosyl)—(1→4)-N-Acetylnormuramoyl-L-α-Aminobutanoyl-D-Isoglutamine”,Carbohydr. Res., vol. 163, pp. 63-72 (1987).
M. Ledvina, et al., “An Alternative Synthesis of O- (2-Acetamido-2-Deoxy-β-D-Glucopyranosyl)—(1→4) -N-Acetylnormuramoyl-L-α-Aminobutanoyl-D-Isoglutamine”,Collect Czech. Chem. Commun., vol. 54, pp. 2784-2794 (1989).
A. Termin, et al., “Synthesis of the GlcNAcβ(1→4) MurNAcβ(1→4) GlcNAcβ(1→4) MurNAc Tetrasaccharide of Bacterial Peptidoglycan”,Liebigs Ann. Chem., pp. 527-533 (1992).
P.H. Gross, et al., “Stereochemically Pure Derivatives of Muramic and Isomuramic Acids”,Justus Liebigs Ann. Chem, pp. 37-45 (1986).
M.P. DeNinno, et al., “A Method for the Selective Reduction of Carbohydrate 4,6-0-Benzylidene Acetals”,Tetrahedron Lett., vol. 36, pp. 669-672 (1995).
G-J Ho, et al., “Carbodiimide-Mediated Amide Formation in a Two-Phase System. A High-Yield and Low-Racemization Procedure for Peptide Synthesis”,J. Org. Chem, 60, pp. 3569-3570 (1995).
M. Imoto, “Total Synthesis ofEscherichia coliLipid A, the Endotoxically Active Principle of Cell-Surface Lipopolysaccharide”,Bull. Chem. Soc. Jpn., vol. 60, pp. 2205-2214 (1987).
A.M. Palache, et al., “Adjuvancy and reactogenicity ofN-acetylglucosaminyl-Nacetylmuramyl-dipeptide (GMDP) orally administered just prior to trivalent influenza subunit vaccine. A double-blind placebo-controlled study in nursing home residents”,Vaccine, vol. 14, pp. 1327-1330 (1996).
R.M. Khaitov, et al., “Immunotherapy of Infectious Postoperative Complications with Glucosaminyl Dipeptide”,Immunotherapy of Infections Ed., pp. 205-211 (1994).
H. Brotz, et al., “The Lantibiotic Mersacidin Inhibits Peptidoglycan Synthesis by Targeting Lipid II”,Antimicrob. Agents Chemother., 42, 154-160 (1998).
Y. Van Heuenoort, et al., “Membrane Intermediates in the Peptidoglycan Metabolism ofEscherichia coli: Possible Roles of PBP 1b and PBP 3”,J. Bacteriol., 174 (11), pp. 3549-3557 (1992).
S. Hitchcock, et al., “The First Total Synthesis of Bacterial Cell Wall Precursor UDP-N-Acetylmuramyl—Pentapeptide (Park Nucleotide)”,J. Am. Chem. Soc., 120, 1916-1917 (1998).
S. Kusumoto, et al., “Synthesis ofN-Acetyl-β-D-Glucosaminyl—(1-4) -N-Acetylmuramyl-L-Alanyl-D-Isoglutamine”,Tetrahedron Lett., No. 45, pp. 4407-4410 (1978).
Whitesides, et al., “Synthesis of Glycosyl Phosphates Using the Fraser-Reid Activation”,J. Org. Chem., vol. 56, pp. 4547-4549 (1991).
Sabesan, et al., “Synthesis of glycosyl phosphates and azides”,Carbohydr. Res., vol. 223, pp. 169-185 (1992).
C. H. Wong, et al., “Synthesis and Use of Glycosyl Phosphites: An Effective Route to Glycosyl Phosphates, Sugar Nucleotides, and Glycosides”,J. Am. Chem. Soc., 115, pp. 2260-2267 (1993).
J.S. Anderson, et al, “Biosynthesis of the Peptidoglycan of Bacterial Cell Walls,”J. Biol. Chem., 242 (13), pp. 3180-3190 (1967).
H.G. Khorana, et al., “The Total Synthesis of Coenzyme A”,J. Am. Chem. Soc., 81, 1265 (1959).
H.G. Khorana, et al., “Nucleoside Polyphosphates. The Synthesis and Some Reactions of Nucleoside-5′ Phosphoromorpholidates and Related Compounds. Improved Methods for the Preparation of Nucleoside-5′ Polyphosphates”,J. Am. Chem. Soc., 83, pp. 649-657 (1961).
H.G. Khorana, et al., “Nucleoside Polyphosphates. An Improved General Method for the Synthesis of Nucleotide Coenzymes. Syntheses of Uridine-5′, Cytidine-5′ and Guanosine-5′ Diphospate Derivatives”,J. Am. Chem. Soc., 83, pp. 659-663 (1961).
J. Wong, et al., “1H-Tetrazole as Catalyst in Phosphomorpholidate Coupling Reactions: Efficient Synthesis of GDP-Fucose, GDP-Mannose, and UDP-Galactose”,J. Org. Chem., 62, 2144-2147 (1997).
Imperiali, et al., “Synthesis of Dolichylpyrophosphate-Linked Oligosaccharides”,Tetrahedron Lett., 31, pp. 6485-6488 (1990).
J. K. Coward, et al., “Synthesis and Evaluation of Synthetic Analogues of Dolichyl-P-P-Chitobiose as Oligosaccharyltransferase Substrates”,Biorg. Med. Chem. Lett., 5, pp. 2701-2706 (1995).
R. W. Jeanloz, et al., Chemical Synthesis of Pyrophosphodiesters of Carbohydrates and Isoprenoid Alcohols. Lipid Intermediates of Bacterial Cell Wall and Antigenic Polysaccharide Biosynthesis,Biochemistry, 11, pp. 2565-2572 (1972).
A. R. Battersby, et al., “Studies on Specific Chemical Fission of Peptide Links. Part I. The Rearrangement of Aspartyl and Glutamyl Peptides”,J. Chem. Soc., 259 pp. 259-269 (1955).
E. Sondheimer, et al., “Imides from Asparagine and Glutamine. II. Alpha-Aminoglutarimide”,J. Am. Chem. Soc., 79, pp. 3767-3770 (1957).
D. Keglevic, et al., “Synthesis and Reactions of O-acetylated benzyl alpha-glycosides of 6-O (2-acetamido-2-deoxy-beta-D-glucopyranosyl) -N-acetylmuramoyl-L-alanyl-D-isoglutamine esters: The Base-Catalysed Isoglutamine • Glutamine Rearrangement in Peptidoglycan-Related Structures”,Carb. Res., 186, pp. 63-75 (1989).
D. Keglevic, et al., “Peptidoglycan-Related Disaccharide-Dipeptides: Differentiation Between Glutaminyl and Isoglutaminyl Residues by NMR Spectroscopy”,J. Carbohydrate Chem., 11, pp. 119-136 (1992).
G. Auger, et al., “Synthesis of an Analogue of the Lipoglycopeptide Membrane Intermediate I of Peptidoglycan Biosynthesis,”Letters In Peptide Science, 4, pp. 371-376 (1997).
B. Schwartz, et al., “Lipid II: Total Synthesis of the Bacterial Cell Wall Precursor and Utilization as a Substrate for Glycosyltransfer and Transpeptidation by Penicillin Binding Protein (PBP) 1b ofEschericia coli,”J. Am. Chem. Soc., 123, pp. 11638-11643 (2001).

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