54769-24-3

Usage

InChI:InChI=1/C21H30N2O5/c1-4-27-20(25)17(13-15(2)3)22-19(24)18-11-8-12-23(18)21(26)28-14-16-9-6-5-7-10-16/h5-7,9-10,15,17-18H,4,8,11-14H2,1-3H3,(H,22,24)/t17-,18-/m0/s1

Upstream product

• 766-09-6 1-ethyl-piperidine 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 2743-40-0 DL-leucine ethyl ester hydrochloride 
• 98807-05-7 Z-Pro-OCamp 
• 2743-60-4 L-Leucine ethyl ester 
• 61-90-5 L-leucine 
• 2743-40-0 L-leucine ethyl ester hydrochloride 
• 54769-31-2 3-methanesulfonyloxy-3H-benzo[d][1,2,3]triazin-4-one 
• 147-85-3 L-proline 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 80143-49-3 N-(1-benzyloxycarbonyl-L-prolyl)-L-leucine hydrazide 
• 5681-02-7 N-(N-(1-benzyloxycarbonyl-L-prolyl]-L-leucyl)-glycine-benzyl ester 
• 2873-36-1 cyclo(L-Pro-L-Leu) 

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.

Synthesis of diketopiperazines containing prolinyl unit - Cyclo(L-prolinyl-L-leucine), cyclo(L-prolinyl-L-isoleucine) and cyclo(L-tryptophyl-L-proline)

Diketopiperazines cyclo(L-prolinyl-L-isoleucine) 4a, cyclo(L-prolinyl-L-leucine) 4b and cyclo(L-tryptophyl-L-proline) 6 were prepared from their respective suitably protected amino acid derivatives by standard peptide chemistry. Cyclo(L-(4-hydroxyprolinyl)-L-phenylalanine) 3, 4a and cyclo(L-prolinyl-L-tyrosine) 5 were tested for their antibacterial activity.

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

Sulfonic acid esters

A novel process for the amidation or esterification which comprises reacting a compound having a carboxy group with a compound having an amino or imino group which can be acylated or with a compound having a hydroxy group in the presence of a sulfonic acid ester of the formula: wherein R1 is an organic group and R2 O-- is a residue of a strongly acidic N-hydroxy compound as a condensation agent, and a novel sulfonic acid ester useful as such a condensation agent and a process for the preparation thereof.