83945-01-1

Upstream product

• 4132-86-9 N-benzyloxycarbonylalanine 
• 5680-79-5 glycine ethyl ester hydrochloride 
• 616-34-2 methoxycarbonylmethylamine 
• 26607-51-2 N-benzyloxycarbonyl-D-alanine 
• 29575-31-3 2-Benzyloxycarbonylamino-propionic acid (2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl ester 
• 29575-31-3 2-Benzyloxycarbonylamino-propionic acid (2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl ester 

Downstream Products

• 34286-66-3 N-benzyloxycarbonyl-(R)alanyl-glycine 
• 145763-51-5 (S)-2-{(S)-2-[2-((R)-2-{2-Benzyloxycarbonylamino-3-[4-(toluene-4-sulfonyloxy)-phenyl]-propionylamino}-propionylamino)-acetylamino]-3-phenyl-propionylamino}-4-methyl-pentanoic acid methyl ester 
• 145763-41-3 N-benzyloxycarbonyl-O-tosyl-(Z)dehydrotyrosyl-(R)alanyl-glycyl-(S)phenylalanyl-(S)leucine methyl ester 
• 83544-70-1 L-tyrosyl-D-alanylglycyl-L-phenylalanyl-L-leucine 2-aminoethylamide 
• 83891-98-9 N-benzyloxycarbonyl-L-tyrosyl-D-alanylglycyl-L-phenylalanyl-L-leucine 2-aminoethylamide 
• 83892-13-1 N-benzyloxycarbonyl-L-tyrosyl-D-alanylglycyl-L-phenylalanyl-L-leucine butylamide 
• 83892-12-0 N-benzyloxycarbonyl-L-tyrosyl-D-alanylglycyl-L-phenylalanyl-L-leucine diethylamide 
• 85148-72-7 N-benzyloxycarbonyl-L-tyrosyl-D-alanylglycyl-L-phenylalanyl-L-leucine hydrazide 
• 83892-11-9 N-benzyloxycarbonyl-L-tyrosyl-D-alanylglycyl-L-phenylalanyl-L-leucine dimethylamide 
• 83892-16-4 N-benzyloxycarbonyl-L-tyrosyl-D-alanylglycyl-L-phenylalanyl-L-leucine methyl ester 
• 83891-97-8 N-benzyloxycarbonyl-L-tyrosyl-D-alanylglycyl-L-phenylalanyl-L-leucine N-methylamine 
• 83891-95-6 L-tyrosyl-D-alanylglycyl-L-phenylalanyl-L-leucine butylamide 
• 67586-37-2 L-tyrosyl-D-alanylglycyl-L-phenylalanyl-L-leucine diethylamide 
• 85148-73-8 L-tyrpsyl-D-alanylglycyl-L-phenylalanyl-L-leucine hydrazide 

Relevant academic research and scientific papers

1,3-Oxazolidin-5-ones derived from proline as chiral components in the synthesis of predictive enantioselective coupling reagents

1,3-Oxazolidin-5-ones derived from both enantiomers of proline and trichloroacetaldehyde were prepared and applied as an amine component in the synthesis of chiral predictive triazine-based coupling reagents. The reagents were found to be useful in condensations yielding enantiomerically enriched products from racemic substrates.

Synthesis of chiral triazine coupling reagents based on esters of n-alkylproline and their application in the enantioselective incorporation of d or l amino acid residue directly from racemic substrate

Esters of N-methylproline and N-allylproline were prepared and used as component for synthesis of chiral triazine based coupling reagents. N-Triazinylammonium tetrafluoroborate obtained from methylester of L-N-methylproline, 2-chloro-4,6-dimethozxy-1,3,5-

Intermolecular Aminolyses of 1-Thioglycosyl Esters of N-Acylamino Acids

Fully acetylated 1-thioglycopyranosyl esters of N-acylamino acids (1-3), comprising different 1-thio sugars, undergo aminolysis with glycine methyl ester in dichloromethane at 40° to form the corresponding N-acyldipeptide methyl esters. The relative reactivity of the C-1 thioester bond towards aminolysis depends inter alia on the structure of the sugar moiety. Acylating efficiency of the 1-thioesters was additionally demonstrated by aminolysis of 2,3,4,6-tetra-O-acetyl-1-S-(N-tert-butyloxycarbonyl-L-tyrosyl)-1-thio-β-D- glucopyranose (3h) with peptidoglycan monomer (PGM, a disaccharide-pentapeptide) in N,N-dimethylformamide at room temperature to give the corresponding disaccharide-hexapeptide.

DIASTEREOSELECTIVE HYDROGENATION OF MONODEHYDRO ENKEPHALINS CONTROLLED BY CHIRAL RHODIUM CATALYSTS

Protected (Z)dehydrophenylalanyl-Leu-enkephalin, (Z)dehydrotyrosyl-Leu-enkephalin and (Z)dehydrotyrosyl-(R)Ala2-Leu-enkephalin, have been synthesized.These compounds have been hydrogenated to give protected Leu-enkephalins in the presence of various chiral rhodium complexes.Deprotection of the product gave Leu-enkephalins or epimers, ytterbium in liquid ammonia allows smooth deprotection of NHCBz or OTs groups on small amounts of peptides.Strong stereocontrol could be achieved by suitable choice of the chiral catalyst.This method has good potential for stereospecific labelling of enkephalins and other small peptides.

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.

OPIOID-LIKE PEPTIDES. PART I. HYDRAZIDE AND SOME AMIDES OF 2-Leu-ENKEPHALIN

Synthesis and pharmacological properties of hydrazide, methylamide, 2-aminoethylamide, dimethylamide and butylamide of 2-Leu-enkephalin are described.