827018-96-2

Upstream product

• 103321-59-1 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-leucine, acid chloride 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 35661-60-0 Fmoc-Leu-OH 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 76542-83-1 Fmoc-Leu-OSu 

Downstream Products

• 38155-10-1 Ac-Leu-Phe-OMe 
• 126402-69-5 (S)-2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-methyl-pentanoylamino]-3-phenyl-propionic acid 
• 38155-18-9 L-leucyl-L-phenylalanine methyl ester 

Relevant academic research and scientific papers

Liquid Phase Peptide Synthesis via One-Pot Nanostar Sieving (PEPSTAR)

Herein, a one-pot liquid phase peptide synthesis featuring iterative addition of amino acids to a “nanostar” support, with organic solvent nanofiltration (OSN) for isolation of the growing peptide after each synthesis cycle is reported. A cycle consists of coupling, Fmoc removal, then sieving out of the reaction by-products via nanofiltration in a reactor-separator, or synthesizer apparatus where no phase or material transfers are required between cycles. The three-armed and monodisperse nanostar facilitates both efficient nanofiltration and real-time reaction monitoring of each process cycle. This enabled the synthesis of peptides more efficiently while retaining the full benefits of liquid phase synthesis. PEPSTAR was validated initially with the synthesis of enkephalin-like model penta- and decapeptides, then octreotate amide and finally octreotate. The crude purities compared favorably to vendor produced samples from solid phase synthesis.

CONTINUOUS, SOLVENT-FREE AND NON-ENZYMATIC PEPTIDE SYNTHESIS BY REACTIVE EXTRUSION

The present disclosure relates to A a continuous, solvent-free and non-enzymatic method for synthesizing a compound of formula (I): Ra-POLYPEP-Rc (I) wherein: POLYPEP is a poly-amino acid compound, Ra and Rc are as specified in the disclosure, which method comprises the steps of: a) feeding an extrusion reactor with (1) a compound of formula (II) Ra-PEPNt-Rg (II) wherein; PEPNt is a mono- or a poly-aminoacid compound, Ra and Rg are as specified in the disclosure, and (2) a compound of formula (III) H-PEPCt-Rc (III) wherein: PEPCt is a mono- or a poly-amino acid compound, and Rc is as defined in the disclosure in the absence of any solvent, so that the compound of formula (II) and the compound of formula (III) react together for generating a compound of formula (I), and b) collecting the compound of formula (I) from the extrusion reactor.

Alternative and chemoselective deprotection of the α-amino and carboxy functions of N-Fmoc-amino acid and N-Fmoc-dipeptide methyl esters by modulation of the molar ratio in the AlCl3/N,N-dimethylaniline reagent system

The amino and carboxy functions in N-Fmoc-α-amino acid and N-Fmoc-peptide methyl esters can be alternatively and chemoselectively deprotected by treatment with the reagent system AlCl3/N,N- dimethylaniline (DMA). The chemoselectivity of the process is controlled by modulating the relative molar ratio of the Lewis acid and DMA. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.