26582-93-4

Upstream product

• 5680-79-5 glycine ethyl ester hydrochloride 
• 35909-82-1 2,3,4,6-tetra-O-benzyl-1-O-(N-tert-butoxycarbonyl-L-phenylalanyl)-β-D-glucopyranose 
• 74293-09-7 2-tert-Butoxycarbonylamino-3-phenyl-propionic acid (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl ester 
• 18942-49-9 Boc-D-Phe-OH 
• 1138-80-3 N-(Benzyloxycarbonyl)glycine 

Downstream Products

• 57224-99-4 Boc-D-phe-glyOH 
• 1610850-93-5 (R)-methyl 2-(2-(tert-butoxycarbonyl(methyl)amino)-N-methyl-3-phenylpropanamido)acetate 

Relevant academic research and scientific papers

Phosphorus pentoxide for amide and peptide bond formation with minimal by-products

Phosphorus pentoxide and DMAP are used for amide bond formation from carboxylic acids and amines. Dipeptides and amides have been synthesized using this reagent in 42–77% yields and >99% ees. The protocol is attractive as it occurs at ambient temperature, the formation of organic by-products is minimal and the reagent can be readily quenched using water. Furthermore, excellent enantioselectivities are observed without the use of harsh triazole based additives.

Aggregation propensity of amyloidogenic and elastomeric dipeptides constituents

This study demonstrates the self-assembly of N- and C-terminal protected dipeptides Phe–Gly and Pro–Gly which were derived from amyloidogenic and elastomeric peptide sequences. These constituents afforded nanostructured supramolecular ensembles through va

Toward the total synthesis of a lagunamide B analogue

Lagunamides, isolated from a marine cyanobacterium Lyngbya majuscule found in Singapore, showed very potent activities against Plasmodium falciparum and murine leukemia cell line (P388). Herein, a concise synthetic approach toward the total synthesis of a lagunamide B analogue is discussed. Macrolactonization, HWE-olefination, and modified Crimmin's aldol are some of the key reactions featured in this synthesis.

Retro peptides, antibodies thereto and their uses for vaccination and in vitro diagnosis

The present invention relates to retro peptides, as well as antibodies thereto, and to their uses, chiefly in the field of preparation of pharmaceutical compositions, in particular vaccines, and for in vitro diagnosis of various pathologies.

PEPTIDE BOND FORMATION BY INTERMOLECULAR AMINOLYSIS OF D-GLUCOPYRANOSYL ESTERS OF AMINO ACIDS

The reaction of HO-protected and -unprotected D-glucopyranosyl esters of N-acylamino acids (Gly, Ala, Phe) with glycine and phenylalanine methyl esters in N,N-dimethylformamide at 38 deg C and dichloromethane at 40 deg C, respectively, led to repture of the C-1 ester bond and formation of the corresponding N-acyldipeptide methyl ester.The relative reactivity of the C-1 ester bond toward aminolysis was greatly influenced by the structure of the amino acid nucleophile, the nature of the aglycon side-chain group, and the anomeric configuration of the D-glucopyranosyl ester involved.Evidence for a substantially lower acylating efficiency of the ester at C-2, as compared to that at C-1, was obtained by aminolysis of two fully acetylated 2-O-(acylaminoacyl)-β-D-glucopyranoses.Treatment of 1-O-(glycylglycylglycyl)-β-D-glucopyranose with phenylalanine methyl ester in N,N-dimethylformamide led to parallel hydrolysis and intermolecular aminolysis, to give the tripeptide and tetrapeptide methyl ester.