53793-17-2

Upstream product

• 56-41-7 L-alanin 
• 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 
• 107292-15-9 p-Nitrobenzyl S-3,6-Diisopropylpyrazin-2-ylthiolcarbonate 
• 107292-12-6 3,6-Diisopropyl-2-p-nitrobenzyloxycarbonyloxypyrazine 

Downstream Products

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

Relevant academic research and scientific papers

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.

p-Nitrobenzyloxycarbonyl (pNZ) as a temporary Na-protecting group in orthogonal solid-phase peptide synthesis - Avoiding diketopiperazine and aspartimide formation

p-Nitrobenzyloxycarbonyl (pNZ) was used as a temporary protecting group for α-amino functionalities in solid-phase peptide synthesis. The corresponding derivatives are readily synthesized solids that perform well on solid phase. The pNZ moiety is orthogonal with the most common protecting groups used in peptide chemistry, and is removed under neutral conditions in the presence of catalytic amounts of acid. The use of pNZ derivatives in conjunction with Fmoc chemistry circumvents typical side reactions associated with the use of piperidine, such as DKP and aspartimide formation. The flexibility of pNZ can be exploited for the preparation of libraries of small organic molecules. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

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.

3,6-Diisopropyl-2-hydroxypyrazine and 3,6-Diisopropyl-2-pyrazinethiol as Carriers of Some Alkoxycarbonyl Groups

Some derivatives of benzyloxycarbonylated 3,6-diisopropyl-2-hydroxypyrazine and 3,6-diisopropyl-2-pyrazinethiol were prepared and shown to be versatile benzyloxycarbonylation reagents for amines and amino acids.It was also ascertained that 3,6-diisopropyl-2-hydroxypyrazine and 3,6-diisopropyl-2-pyrazinethiol serve effectively as carriers of the β,β,β-trichloroethoxycarbonyl group.