678159-15-4

Upstream product

• 545-06-2 trichloroacetonitrile 
• 678159-14-3 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranose 
• 766-39-2 2,3-Dimethylmaleic anhydride 
• 90-76-6 2-deoxy-2-amino glucose 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 216877-47-3 tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleoylamido-glucopyranoside 
• 340290-23-5 tert-butyldimethylsilyl 3,4,6-tri-O-acetyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside 
• 216877-35-9 tert-butyldimethylsilyl 2-deoxy-2-dimethylmaleoyl-β-D-glucopyranoside 
• 216877-67-7 tert-butyldimethylsilyl 4,6-O-benzylidene-2-deoxy-2-dimethylmaleoyl-β-D-glucopyranoside 
• 216876-40-3 tert-butyldimethylsilyl 3,4,6-tri-O-acetyl-2-deoxy-2-dimethylmaleoyl-β-D-glucopyranoside 
• 678159-10-9 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranose 
• 666728-53-6 Acetic acid (3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-(3,4-dimethyl-2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-tetrahydro-pyran-4-yl ester 
• 678159-09-6 tert-butyldimethylsilyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside 
• 678159-06-3 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl trichloroacetimidate 

Downstream Products

• 678159-17-6 methyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside 
• 678159-16-5 methyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside 

Relevant academic research and scientific papers

Deciphering the Nature of Enzymatic Modifications of Bacterial Cell Walls

The major constituent of bacterial cell walls is peptidoglycan, which, in its crosslinked form, is a polymer of considerable complexity that encases the entire bacterium. A functional cell wall is indispensable for survival of the organism. There are several dozen enzymes that assemble and disassemble the peptidoglycan dynamically within each bacterial generation. Understanding of the nature of these transformations is critical knowledge for these events. Octasaccharide peptidoglycans were prepared and studied with seven recombinant cell-wall-active enzymes (SltB1, MltB, RlpA, mutanolysin, AmpDh2, AmpDh3, and PBP5). With the use of highly sensitive mass spectrometry methods, we described the breadth of reactions that these enzymes catalyzed with peptidoglycan and shed light on the nature of the cell wall alteration performed by these enzymes. The enzymes exhibit broadly distinct preferences for their substrate peptidoglycans in the reactions that they catalyze.

Synthesis of a Fragment of Bacterial Cell Wall

Cell wall is indispensable for survival of bacteria. This large molecular "mesh" encases the entire cytoplasm of bacteria, and it is comprised of repeating backbone units of N-acetyl-glucosamine (NAG)-N-acetyl-muramic acid (NAM). A pentapeptide is attached to each of the lactyl units of the N-acetyl-muramic acid. The cell wall has both cross-linked and non-cross-linked components. In the present paper, we have devised a synthetic route for the preparation of a fragment of the cell wall comprised of a tetrasaccharide (NAG-NAM-NAG-NAM), along with the two appended peptides. We also report the syntheses of three glycosyl donors (compounds 5, 7, and 9) and three glycosyl acceptors (compounds 4, 6, and 8) based on the D-glucosamine structure as a building unit. The synthetic strategy that is disclosed is generally useful in construction of other natural products containing the D-glucosamine as a building block.