55739-16-7

Upstream product

• 617-27-6 DL-alanine ethyl ester hydrochloride 
• 98807-06-8 Z-Val-OCamp 
• 501-53-1 benzyl chloroformate 
• 72-18-4 L-valine 
• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 64-17-5 ethanol 
• 17445-33-9 (S)-2-((S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanamido)propanoic acid 
• 1115-59-9 (S)-alanine ethyl ester hydrochloride 
• 133010-20-5 Cbz-Val-F 
• 54647-77-7 N-[(benzyloxy)carbonyl]-L-valine, compound with dicyclohexylamine (1:1) 
• 3082-75-5 L-Alanine ethyl ester 

Downstream Products

• 1115-74-8 Val-Ala 
• 97800-71-0 1-Benzyl-3-[(S)-1-((S)-1-carbamoyl-ethylcarbamoyl)-2-methyl-propylcarbamoyl]-pyridinium; bromide 
• 17445-33-9 (S)-2-((S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanamido)propanoic acid 

Relevant academic research and scientific papers

Tandem deprotection/coupling for peptide synthesis in water at room temperature

A tandem deprotection/coupling sequence is reported for solution-phase peptide synthesis in water under micellar catalysis conditions using the designer surfactant TPGS-750-M. Cbz deprotection followed by peptide coupling in the presence of COMU and 2,6-lutidine afforded polypeptides containing up to 10 amino acid residues. A broad scope characterizes this new technology. No epimerization has been detected. The associated E Factors, as a measure of "greenness" and known to be extremely high for peptide couplings, have been reduced to less than 10 due to the step-economy and minimal amounts of organic solvent needed for product extraction.

Papain-catalyzed esterification of N(α)-protected amino acids and dipeptides with ethanol in different organic systems

The papain-catalyzed esterification of N(α)-protected amino acids and dipeptides with ethanol in mostly hydrophobic organic solvent systems containing low amounts of water has been investigated. The influence of various parameters, such as the amount of added water, reaction time, temperature and pH of added buffer, on the yield of ester was studied first on the model substrate Z-Ala. The optimized reaction conditions were then used for esterification of a series of N(α)-protected amino acids and dipeptides.

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.

KINETICS OF THE ALKALINE HYDROLYSIS OF SEVERAL N-BENZYLOXYCARBONYLDIPEPTIDE METHYL AND ETHYL ESTERS

The reaction rates of the alkaline hydrolysis of synthesized N-protected dipeptide methyl and ethyl esters were studied systematically.From the kinetic data the energies of activation, the pre-exponential factors and the reference values at 40 deg C were calculated.The rate of hydrolysis shows to be strongly dependent on the C-terminal amino acid in the sequence Gly >> Ala/Met/Phe > Leu >> Val/Pro.Surprisingly the N-terminal amino acid also exerts an effect, but in a different sequence.N-Terminal Phe in particular shows a relative accelerating effect.Remarkable is the significantly faster ester hydrolysis of glycine containing dipeptide ethyl esters in ethanol/water compared to the corresponding methyl esters in methanol/water.

ENANTIOSELECTIVE SYNTHESIS OF PEPTIDES USING (1R)-3-HYDROXY-1,8,8-TRIMETHYL-3-AZABICYCLOOCTANE-2,4-DIONE ((+)-N-HYDROXYCAMPHORIMIDE) AN ACTIVE ESTER GROUP

The enantioselective coupling reaction of N-protected amino acid (+)-N-hydroxycamphorimide esters (-OCamp) with racemic amino acid esters is discussed.The coupling reaction of several amino acids showed high enantioselectivity.Keywords-enantioselective synthesis; (+)-N-hydroxycamphorimide; peptide, active ester; coupling reaction

Investigations on Quaternary Pyridinium Salts, XVIII. - Note on Synthetic Cyclopeptides with 1,4-Dihydronicotinamide Moiety

Quaternary salts of the amides of N-nicotinoyldipeptides form under the influence of base dimers with 20-membered rings, cyclopeptide-like substances with two 1,4-dihydronicotinamide moieties (8).

CLEAVAGE OF 4-PYRIDYLGLYCINE DERIVATIVES BY Ni(II)-PHTHALOCYANINE CATALYSED AUTOOXIDATION - MODEL EXPERIMENTS FOR PEPTIDE SEGMENT COUPLING BY FOUR COMPONENT CONDENSATIONS

The four component condensation of 4-pyridinecarboxaldehyde and aliphatic isonitriles with suitable protected α-amino acid derivatives yields products which can be cleaved by oxygen in the presence of nickel(II)-phthalocyanine into elongated peptide derivatives.