102988-93-2

Upstream product

• 26607-51-2 N-benzyloxycarbonyl-D-alanine 
• 543-27-1 isobutyl chloroformate 

Downstream Products

• 111633-10-4 {(R)-1-[Methyl-(3-phenyl-propyl)-carbamoyl]-ethyl}-carbamic acid benzyl ester 
• 148205-70-3 Z-D-Ala-Pro-Arg(NO₂)-Pro-OBzl 
• 68223-06-3 (3-diazo-1-(R)-methyl-2-oxopropyl)carbamic acid benzyl ester 
• 177283-75-9 dibenzyl ((2R,3S,4S,5R)-3,4-bis((2-(trimethylsilyl)ethoxy)methoxy)hexane-2,5-diyl)dicarbamate 
• 177283-74-8 dibenzyl ((2R,3S,4S,5R)-3,4-dihydroxyhexane-2,5-diyl)dicarbamate 
• 105499-10-3 (R)-benzyl-(1-methyl-2-oxoethyl)carbamate 
• 34276-31-8 benzyl N-[(1R)-1-(1H-1,2,3,4-tetrazol-5-yl)ethyl]carbamate 
• 176894-58-9 (2R)-2-(benzyloxycarbonylamino)propionitrile 
• 151378-81-3 benzyl [(1R)-2-amino-1-methyl-2-oxoethyl]carbamate 
• 22209-85-4 (2S,2'R)-N-(N-Benzyloxycarbonylalanyl)proline methyl ester 
• 152169-60-3 benzyl {(2R)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl}carbamate 
• 148205-73-6 Z-D-Ala-Pro-Arg(NO₂)-Val-OBzl 
• 129474-02-8 Cbz-D-Ala-L-Pro-NH₂ 

Relevant academic research and scientific papers

Synthesis and characterization of chiral di(N-protected-α-amino) diazo-β-diketones from α-diazoketones and imidazolides derived from amino acids

Di(N-protected-α-amino)diazo-β-diketones were prepared by the reaction of activated N-protected-α-amino acids (imidazolides) with α-diazoketones, derived from natural amino acids, in the presence of lithium diisopropylamide in tetrahydrofuran as the solvent at -78 °C.

Frakefamide, an analgesic tetrapeptide: Development of a pilot-plant-scale process

A pilot-plant-process is described where frakefamide × HCl (L-tyrosyl-D-alanyl-p-fluoro-L-phenylalanyl-L-phenylalanin-amide hydrochloride) was synthesised from its amino acid monomers in seven steps. The synthesis was performed in 70-L equipment, and the

Design and synthesis of cyclopenta[g]quinazoline-based antifolates as inhibitors of thymidylate synthase and potential antitumor agents

Following the development of raltitrexed, the synthesis of nonpolyglutamatable inhibitors of TS that do not use the reduced folate carrier (RFC) for cellular entry should provide compounds which overcome mechanisms of resistance to folate-based inhibitors

Synthesis of fused 1,2,5-triazepine-1,5-diones and some N2- and N3-substituted derivatives: Potential conformational mimetics for cis-peptidyl prolinamides

The synthesis of a new fused 1,2,5-triazepine-1,5-dione heterocycle, which is expected to mimic structural features of cis-peptldyl prolinamides, is described. The required parent heterocycle, corresponding to cis-glycy-(2S)-prolinamide, has been prepared in good yield by the cyclisation of N-(2-bromoacetylprolyl)-hydrazine which is itself generated in situ from the bromoacetyl proline methyl ester. Analogues corresponding to cis-(2R)-alanyl- and cis-(2S)-alanyl-(2S)-prolinamide have been similarly prepared from the appropriate N-(2-bromopropionyl)proline methyl esters and hydrazine hydrate where the cyclisation step, involving the displacement of bromide, has been shown to occur with inversion of configuration at C-2 of the propionyl moiety. Acylation at the N-3 position of the triazepine is equivalent to N-terminal acylation of the residue preceding the proline residue in cis-aminoacyl prolinamides. This has been achieved without incident using standard peptide coupling procedures. Extension at the 'C-terminal' has been achieved by preparing elaborated hydrazine precursors which are reacted with suitably activated esters of N-α-halogenoacylprolines, prior to cyclisation, to give the required fused triazepine dione. Thus it is possible to prepare constrained cis-peptidyl prolyl peptide mimetics of defined stereochemistry based upon this new triazepine dione in which all of the non-proline residues can be varied.

Preparation and structure-activity relationship of novel P1/P1'- substituted cyclic urea-based human immunodeficiency virus type-1 protease inhibitors

A series of novel P1/P1'-substituted cyclic urea-based HIV-1 protease inhibitors was prepared. Three different synthetic schemes were used to assemble these compounds. The first approach uses amino acid-based starting materials and was originally used to prepare DMP 323. The other two approaches use L-tartaric acid or L-mannitol as the starting material. The required four contiguous R,S,S,R centers of the cyclic urea scaffold are introduced using substrate control methodology. Each approach has specific advantages based on the desired P1/P1' substituent. Designing analogs based on the enzyme's natural substrates provided compounds with reduced activity. Attempts at exploiting hydrogen bond sites in the S1/S1' pocket, suggested by molecular modeling studies, were not fruitful. Several analogs had better binding affinity compared to our initial leads. Modulating the compound's physical properties led to a 10-fold improvement in translation resulting in better overall antiviral activity.

Enkephalin analogs as systemically active antinociceptive agents: O- and N-alkylated derivatives of the dipeptide amide L-2,6-dimethyltyrosyl-N-(3- phenylpropyl)-D-alaninamide

A number of O- and N-alkylated derivatives of the antinociceptive, orally active, μ-opioid-selective truncated enkephalin analog L-2,6- dimethyltyrosyl-N-(3-phenylpropyl)-D-alaninamide (2,SC-39566) were synthesized to explore the structure-activity relati

Amino acids and peptides. XVI. Synthesis of N-terminal tetrapeptide analogs of fibrin α-chain and their inhibitory effects on fibrinogen/thrombin clotting

N-Terminal tetrapeptide analogs of fibrin α-chain were synthesized by the solution method using a new active ester, the ester of the oxime of p-nitroacetophenone, and by the solid-phase method. Their inhibitory effects on fibrinogen/thrombin clotting were examined. Of the synthetic peptides, amide analogs of Gly-Pro-Arg-Pro exhibited a more potent inhibitory effect.