281666-44-2

Usage

Uses

Used in Pharmaceutical Industry:
(2S,4S)-1-(BENZYLOXYCARBONYL)-4-(TERT-BUTOXYCARBONYLAMINO)PYRROLIDINE-2-CARBOXYLIC ACID is used as a key intermediate in the synthesis of complex peptides and other biologically active molecules, contributing to the development of new drugs and therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, (2S,4S)-1-(BENZYLOXYCARBONYL)-4-(TERT-BUTOXYCARBONYLAMINO)PYRROLIDINE-2-CARBOXYLIC ACID is utilized as a versatile building block for creating a variety of chemical compounds, taking advantage of its protective groups and stereochemistry to control reaction selectivity and outcomes.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 281666-43-1 4-amino-N-benzyloxycarbonyl-L-cis-proline 
• 168263-80-7 methyl (2S,4S)-1-benzyloxycarbonyl-4-tert-butoxycarbonylaminopyrrolidine-2-carboxylate 

Downstream Products

• 1279034-78-4 (2S,4S)-4-tert-Butoxycarbonylamino-pyrrolidine-2-carboxylic acid 

Relevant academic research and scientific papers

Discovery and synthesis of HIV integrase inhibitors: Development of potent and orally bioavailable N-methyl pyrimidones

The human immunodeficiency virus type-1 (HIV-1) encodes three enzymes essential for viral replication: a reverse transcriptase, a protease, and an integrase. The latter is responsible for the integration of the viral genome into the human genome and, therefore, represents an attractive target for chemotherapeutic intervention against AIDS. A drug based on this mechanism has not yet been approved. Benzyl-dihydroxypyrimidine-carboxamides were discovered in our laboratories as a novel and metabolically stable class of agents that exhibits potent inhibition of the HIV integrase strand transfer step. Further efforts led to very potent compounds based on the structurally related N-Me pyrimidone scaffold. One of the more interesting compounds in this series is the 2-N-Me-morpholino derivative 27a, which shows a CIC95 of 65 nM in the cell in the presence of serum. The compound has favorable pharmacokinetic properties in three preclinical species and shows no liabilities in several counterscreening assays.

Synthesis of alanine and proline amino acids with amino or guanidinium substitution on the side chain

Competitive binding of peptides containing basic amino acids to disrupt or prevent the Tat-TAR interaction could result in diminished transcription as well as translation and hence constitutes an alternative way of controlling HIV replication. Therefore, we synthesized guanidinium and amino containing amino acids, based on a proline or an alanine scaffold. The introduction of the guanidinium moiety was best accomplished using 1H- pyrazole-1-carboxamidine hydrochloride, with Pmc used for its protection. The absence of racemization, maintained throughout the whole synthesis, was confirmed by chiral purity determination. These building blocks were smoothly incorporated into oligopeptides, which proved their suitability for use in a combinatorial approach for selecting TAR binding ligands. (C) 2000 Elsevier Science Ltd.