53793-17-2

Basic information

• Product Name: PNZ-L-ALANINE
• Synonyms: PNZ-L-ALANINE;PNZ - ALANINE
• CAS NO: 53793-17-2
• Molecular Formula: C₁₁H₁₂N₂O₆
• Molecular Weight: 268.22
• Mol File: 53793-17-2.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: PNZ-L-ALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: PNZ-L-ALANINE(53793-17-2)
• EPA Substance Registry System: PNZ-L-ALANINE(53793-17-2)

Safety Data

• Hazardous Substances Data: 53793-17-2(Hazardous Substances Data)

Upstream product

• 56-41-7 L-alanin 
• 107292-12-6 3,6-Diisopropyl-2-p-nitrobenzyloxycarbonyloxypyrazine 
• 107292-15-9 p-Nitrobenzyl S-3,6-Diisopropylpyrazin-2-ylthiolcarbonate 
• 158556-65-1 4-nitrophenyl (4-nitrophenyl)methyl carbonate 
• 71731-66-3 4-nitrobenzyl carbonazidate 
• 4457-32-3 4-nitrobenzyl chloroformate 
• 619-73-8 4-nitrobenzyl chloride 

Downstream Products

• 161855-71-6 (S)-2-(4-Nitro-benzyloxycarbonylamino)-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester 

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.

Peptidic prodrugs of novel aminomethyl-THF 1β-methylcarbapenems

Peptidic prodrugs of the five most active aminomethyl-THF β- methylcarbapenems were synthesized. Of these, only L-amino acid derivatives from la demonstrated an improved oral activity. These results indicate that the L-amino acid derivatives from la are orally absorbed most likely through the dipeptide and tripeptide transport mechanism.