133010-19-2

Upstream product

• 49760-60-3 N-benzyloxycarbonyl-L-alanyl chloride 
• 1142-20-7 N-Cbz-Ala 

Downstream Products

• 175028-30-5 (2S,5S)-1-((S)-2-Benzyloxycarbonylamino-propionyl)-5-(2-methyl-propenyl)-pyrrolidine-2-carboxylic acid methyl ester 
• 1604809-95-1 Z-Ala-Azt(tBu)-Ala-OMe, Azt - 3-aminoazetidine-3-carboxylic acid 
• 1604809-96-2 Z-Ala-Azt(tAmyl)-Ala-OMe, Azt - 3-aminoazetidine-3-carboxylic acid 
• 2483-51-4 N-[(benzyloxy)carbonyl]-L-alanyl-L-alanine methyl ester 
• 1025926-75-3 [(S)-2-((S)-1-Carbamoyl-3,4-dihydro-1H-isoquinolin-2-yl)-1-methyl-2-oxo-ethyl]-carbamic acid benzyl ester 
• 539020-74-1 [(S)-2-((S)-1-Cyano-1H-isoquinolin-2-yl)-1-methyl-2-oxo-ethyl]-carbamic acid benzyl ester 
• 439589-15-8 (S)-2-Benzyloxycarbonylamino-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 2503-32-4 ethyl N-(benzyloxycarbonyl)-L-alanylglycinate 

Relevant academic research and scientific papers

Synthesis of Optically Active 2-Amino-1,3,4-oxadiazoles and their Hybrid Peptides

Synthesis of 2-amino-1,3,4-oxadiazole derivatives of Nα-Cbz(benzyloxycarbonyl)/Boc-protected amino/peptide acids under sonication is described. The conditions involved in the present protocol are simple, mild, and racemization free. The utility

Metal-free approach for hindered amide-bond formation with hypervalent iodine(iii) reagents: application to hindered peptide synthesis

A new bio-inspired approach is reported for amide and peptide synthesis using α-amino esters that possess a potential activating group (PAG) at the ester residue. To activate the ester functionality under mild metal-free conditions, we exploited the facile dearomatization of phenols with hypervalent iodine(iii) reagents. Using a pyridine-hydrogen fluoride complex, highly reactive acyl fluoride intermediates can be successfully generated, thereby allowing for the smooth formation of sterically hindered amides and peptides from bulky amines and α-amino esters, respectively.

Synthesis and conformational study of model peptides containing N-substituted 3-aminoazetidine-3-carboxylic acids

Model peptides containing N-substituted 3-aminoazetidine-3-carboxylic acids have been synthesized to investigate the conformational features of these Cα-tetrasubstituted amino acids. The target peptides were designed and prepared by classical synthetic methods in solution, exploiting the convenient N-substituted 3-azidoazetidine-3-carboxylic acids as precursors. The conformational preferences of the newly synthesized peptides were investigated in solution by IR and NMR spectroscopy. It was observed that the 3-aminoazetidine-3-carboxylic acid moiety is likely a β-turn inducer. In addition, an interesting main-chain-to-side-chain hydrogen bond that forms a six-membered pseudo-cycle was detected. It connects the nitrogen (acceptor) of the azetidine ring to the amide NH (donor) of the immediately following residue. This unexpected hydrogen bond increases the number of conformational options offered by N-substituted 3-aminoazetidine-3-carboxylic acids when designing foldamers with new and predictable 3D structures.

A convenient, one-pot procedure for the preparation of acyl and sulfonyl fluorides using Cl3CCN, Ph3P, and TBAF(t -BuOH) 4

Various carboxylic acids were converted into acyl fluorides in excellent yields by treatment with trichloroacetonitrile, triphenylphosphine, and TBAF(t-BuOH)4 at room temperature. The reaction was applicable to the preparation of acid-sensitive amino acid fluorides without deprotection or rearrangement

Synthesis of Boc- and Z-protected amino acid fluorides employing DAST as a fluorinating agent

DAST [(diethylamino)sulphur trifluoride] has been used as a fluorinating agent for the synthesis of Boc- and Z-protected amino acid fluorides. All the compounds made have been isolated as crystalline solids in good yield and purity.

Amino acid fluorides: Their preparation and use in peptide synthesis

Z or Fmoc amino acid fluorides have been prepared from the protected amino acids and cyanuric fluoride, and have been tested both in the condensation with simple amino acid esters and in Solid Phase Peptide Synthesis.

tert-Butyloxycarbonyl and Benzyloxycarbonyl Amino Acid Fluorides. New, Stable Rapid-Acting Acylating Agents for Peptide Synthesis

A new class of rapid-acting acylating agents, α-BOC and Z amino acid fluorides are obtained as stable, often crystalline, compounds by treatment of the protected amino acid cyanuric fluoride.