1006693-86-2

Basic information

• Product Name: C₂₉H₃₂N₂O₆
• Synonyms: C₂₉H₃₂N₂O₆
• CAS NO: 1006693-86-2
• Molecular Weight: 504.583
• Mol File: 1006693-86-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: C₂₉H₃₂N₂O₆(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₉H₃₂N₂O₆(1006693-86-2)
• EPA Substance Registry System: C₂₉H₃₂N₂O₆(1006693-86-2)

Safety Data

• Hazardous Substances Data: 1006693-86-2(Hazardous Substances Data)

Upstream product

• 914981-83-2 dibenzyl (2S,6R)-6-[{(benzyloxy)carbonyl}amino]-2-{(tertbutyloxycarbonyl)amino}heptanedioate 
• 1104583-26-7 (2S,6R)-6-[{(benzyloxy)carbonyl}amino]-2-{(tert-butyloxycarbonyl)amino}heptanedioic acid 
• 91216-98-7 2,6-Bis-acetylamino-heptanedioic acid 
• 1104583-42-7 benzyl (2R,6S)-2-(benzyloxycarbonylamino)-6-(tert-butoxycarbonylamino)-7-hydroxyheptanoate 
• 1423076-21-4 (S)-(tert-butyl) 4-((R)-5-(benzyloxy)-4-(benzyloxycarbonylamino)-5-oxopentyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 167466-67-3 (R)-benzyl 2-(((benzyloxy)carbonyl)amino)pent-4-enoate 

Downstream Products

• 1423076-23-6 (2S,6R)-dibenzyl 2-((R)-4-amino-5-(benzyloxy)-5-oxopentanamido)-6-(benzyloxycarbonylamino)heptanedioate 
• 1423076-24-7 (2S,6R)-dibenzyl 2-((R)-4-heptanecarbonylamino-5-(benzyloxy)-5-oxopentanamido)-6-(benzyloxycarbonylamino)heptanedioate 
• 1423076-25-8 (2S,6R)-dibenzyl 2-((R)-4-tridecanecarbonylamino-5-(benzyloxy)-5-oxopentanamido)-6-(benzyloxycarbonylamino)heptanedioate 
• 1423076-22-5 (2S,6R)-dibenzyl 2-((R)-4-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-(benzyloxy)-5-oxopentanamido)-6-(benzyloxycarbonylamino)heptanedioate 

Relevant articles and documents

Synthesis of characteristic Mycobacterium peptidoglycan (PGN) fragments utilizing with chemoenzymatic preparation of meso-diaminopimelic acid (DAP), and their modulation of innate immune responses

Peptidoglycan (PGN) is a major component of bacterial cell wall and is recognized as a potent immunostimulant. The PGN in the cell envelope of Mycobacterium Tuberculosis has been shown to possess several unique characteristics including the presence of N-glycolyl groups (in addition to N-acetyl groups) in the muramic acid residues, and amidation of the free carboxylic acid of d-Glu or of meso-DAP in the peptide chains. Using a newly developed, highly stereoselective, chemoenzymatic approach for the synthesis of meso-DAP in peptide stems, we successfully synthesized for the first time, a series of Mycobacterium PGN fragments that include both mono- and disaccharides of MurNGlyc or 1,6-anhydro-MurNGlyc, as well as peptide-amidated variants. The ability of these PGN fragments to stimulate the immune system through activation of human Nod1 and Nod2 was examined. The PGN fragments were found to modulate immune stimulation, specifically, amidation at the d-Glu and meso-DAP in the peptide stem strongly reduced hNod1 activation. This effect was dependent on modification position. Additionally, N-glycolyl (instead of acetyl) of muramic acid was associated with slightly reduced human Nod1 and Nod2 stimulatory capabilities.

Synthesis of diaminopimelic acid containing peptidoglycan fragments and tracheal cytotoxin (TCT) and investigation of their biological functions

Bacterial cell wall peptidoglycan (PGN) is a potent immunostimulator and immune adjuvant. The PGN of Gram-negative bacteria and some Gram-positive bacteria contain meso-diaminopimelic acid (meso-DAP), and we have recently shown that the intracellular protein Nodi is a PGN receptor and recognizes DAPcontaining peptides. In this study, we achieved the synthesis of DAP-containing PGN fragments, including the first chemical synthesis of tracheal cytotoxin (TCT), GlcNAc-(β1-4)-(anhydro) Mur-NAc-L-Ala-γ-D-Glu-meso- DAP-D-Ala, and a repeating-unit of DAP-type PGN, GlcNAc-(β1-4)-MurNAc-L- Ala-γ-D-Glu-meso-DAP-D-Ala. For the synthesis of PGN fragments, we first established a new synthetic method for an orthogonally protected meso-DAP derivative, and then we constructed the glycopeptide structures. The ability of these fragments to stimulate human Nodi, as well as differences in Nodi recognition of the variety of synthesized ligand structures were examined. The results showed that the substitution of the N terminus of iE-DAP is necessary for stronger Nodi recognition, but the structure of the substituent seems not to be strictly recognized. The importance of the carboxyl group at the 2-position of DAP for human Nod1 stimulation was also shown.