18800-73-2

Basic information

• Product Name: Pentanoic acid, 5-amino-4-[[(1,1-dimethylethoxy)carbonyl]amino]-5-oxo-, phenylmethyl ester, (S)-
• CAS NO: 18800-73-2
• Molecular Formula: C17H24N2O5
• Molecular Weight: 336.388
• Mol File: 18800-73-2.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: Pentanoic acid, 5-amino-4-[[(1,1-dimethylethoxy)carbonyl]amino]-5-oxo-, phenylmethyl ester, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Pentanoic acid, 5-amino-4-[[(1,1-dimethylethoxy)carbonyl]amino]-5-oxo-, phenylmethyl ester, (S)-(18800-73-2)
• EPA Substance Registry System: Pentanoic acid, 5-amino-4-[[(1,1-dimethylethoxy)carbonyl]amino]-5-oxo-, phenylmethyl ester, (S)-(18800-73-2)

Safety Data

• Hazardous Substances Data: 18800-73-2(Hazardous Substances Data)

Upstream product

• 1676-73-9 L-glutamic acid γ-benzyl ester 
• 24608-52-4 tert-butyl chloroformate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 35793-73-8 N-(tert-butyloxycarbonyl)-γ-benzyl-D-glutamic acid 
• 541-41-3 chloroformic acid ethyl ester 
• 100-39-0 benzyl bromide 
• 55297-72-8 (R)-5-amino-4-((tert-butoxycarbonyl)amino)-5-oxopentanoic acid 
• 63648-73-7 N-benzyloxycarbonyl-D-glutamic acid 
• 41840-28-2 S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine 
• 100-51-6 benzyl alcohol 
• 2578-33-8 D-glutamic acid-5-benzyl ester 
• 870-46-2 t-butoxycarbonylhydrazine 
• 6893-26-1 D-Glutamic acid 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 

Downstream Products

• 104090-94-0 L-4-(benzyloxycarbonyl)-2-(t-butyloxycarbonylamino)thiobutyramide 
• 80064-48-8 γ-benzyl-glutamic acid amide 
• 80143-17-5 (R)-1-amino-5-(benzyloxy)-1,5-dioxopentan-2-aminium 2,2,2-trifluoroacetate 
• 71811-14-8 D-Glutaminsaeure-α-amid-γ-benzylester 
• 18800-75-4 Glu(OBn)-NH₂ hydrochloride 
• 19522-40-8 D-α-glutamine 
• 292150-20-0 N-Fmoc-D-isoglutamine 
• 131148-65-7 ethyl L-2-<3-(benzyloxycarbonyl)-1-(t-butyloxycarbonylamino)propyl>thiazole-4-carboxylate 
• 1120367-12-5 N-tert-butyloxycarbonyl-O-benzyl glutamic nitrile 
• 66025-93-2 (S)-1-(((R)-1-amino-5-(benzyloxy)-1,5-dioxopentan-2-yl)amino)-1-oxopropan-2-aminium 2,2,2-trifluoroacetate 
• 69323-69-9 benzyl (R)-4-((S)-2-((R)-2-(((4aR,6S,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanamido)propanamido)-5-amino-5-oxopentanoate 
• 62928-83-0 benzyl (R)-4-((S)-2-((R)-2-(((2S,3R,4R,5S,6R)-3-acetamido-2-(benzyloxy)-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)propanamido)propanamido)-5-amino-5-oxopentanoate 

Relevant articles and documents

Synthesis of Carbapenems Containing Peptidoglycan Mimetics and Inhibition of the Cross-Linking Activity of a Transpeptidase of l,d Specificity

The carbapenem class of β-lactams has been optimized against Gram-negative bacteria producing extended-spectrum β-lactamases by introducing substituents at position C2. Carbapenems are currently investigated for the treatment of tuberculosis as these drugs are potent covalent inhibitors of l,d-transpeptidases involved in mycobacterial cell wall assembly. The optimization of carbapenems for inactivation of these unusual targets is sought herein by exploiting the nucleophilicity of the C8 hydroxyl group to introduce chemical diversity. As β-lactams are structure analogs of peptidoglycan precursors, the substituents were chosen to increase similarity between the drug and the substrate. Fourteen peptido-carbapenems were efficiently synthesized. They were more effective than the reference drug, meropenem, owing to the positive impact of a phenethylthio substituent introduced at position C2 but the peptidomimetics added at position C8 did not further improve the activity. Thus, position C8 can be modified to modulate the pharmacokinetic properties of highly efficient carbapenems.

Critical Impact of Peptidoglycan Precursor Amidation on the Activity of l,d-Transpeptidases from Enterococcus faecium and Mycobacterium tuberculosis

The bacterial cell wall peptidoglycan contains unusual l- and d-amino acids assembled as branched peptides. Insight into the biosynthesis of the polymer has been hampered by limited access to substrates and to suitable polymerization assays. Here we report the full synthesis of the peptide stem of peptidoglycan precursors from two pathogenic bacteria, Enterococcus faecium and Mycobacterium tuberculosis, and the development of a sensitive post-derivatization assay for their cross-linking by l,d-transpeptidases. Access to series of stem peptides showed that amidation of free carboxyl groups is essential for optimal enzyme activity, in particular the amidation of diaminopimelate (DAP) residues for the cross-linking activity of the l,d-transpeptidase LdtMt2 from M. tuberculosis. Accordingly, construction of a conditional mutant established the essential role of AsnB indicating that this DAP amidotransferase is an attractive target for the development of anti-mycobacterial drugs.

NOVEL MURAMYL PEPTIDE DERIVATIVE COMPOUND, SYNTHESIS AND USES THEREOF

The invention relates to novel Muramyl Dipeptide (MDP) derivative compound of structural Formula-VIII, a process for synthesis, intermediates used in the synthesis and use thereof. R = alkyl (both linear and branched), aryl, substituted aryl, alkoxy alkyl Wherein, R can be both linear and branched alkyl, aryl, substituted aryl and alkoxy alkyl. These compounds possess excellent pharmacological properties, in particular immunomodulating properties for use as adjuvant in vaccine formulations. These compounds are, particularly useful as adjuvants in vaccines.