95015-69-3

Upstream product

• 86827-18-1 N-benzyloxycarbonyl-O-benzyl-L-tyrosine 
• 7440-44-0 pyrographite 
• 74-88-4 methyl iodide 
• 225386-51-6 phenylmethyl (4S)-5-oxo-4-({4-[(phenylmethyl)oxy]phenyl}methyl)-1,3-oxazolidine-3-carboxylate 

Downstream Products

• 205874-82-4 N^α-benzyloxycarbonyl-N^α-methyl-O-benzyltyrosyl-N^g-tosylarginyl-N^α-methyl-N^g-tosylarginyl-D-leucine benzyl ester 
• 95015-80-8 5-{[(S)-3-(4-Hydroxy-phenyl)-2-methylamino-propionyl]-methyl-amino}-pentanoic acid methyl-phenethyl-amide; hydrochloride 
• 205874-81-3 N-(N^α-benzyloxycarbonyl-N^α-methyl-O-benzyltyrosyl-N^g-tosylarginyl-N^α-methyl-N^g-tosylarginyl-D-leucyl)ethanamine 
• 205874-83-5 N¹-benzyloxycarbonyl-N⁸-(N^α-benzyloxycarbonyl-N^α-methyl-O-benzyltyrosylleucyl-N^α-methyl-N^g-nitroarginyl-D-leucyl)-1,8-octanediamine 
• 205874-96-0 N¹-benzyloxycarbonyl-N⁸-(N^α-benzyloxycarbonyl-N^α-methyl-O-benzyltyrosylleucyl-D-leucyl-D-leucyl)-1,8-octanediamine 
• 175216-34-9 N¹-benzyloxycarbonyl-N⁸-(N^α-benzyloxycarbonyl-N^α-methyl-O-benzyltyrosyl-N^g-tosylarginyl)-1,8-octanediamine 
• 205874-97-1 N¹-benzyloxycarbonyl-N⁵-(N^α-benzyloxycarbonyl-N^α-methyl-O-benzyltyrosyl-N^g-tosylarginyl)-1,5-pentanediamine 
• 205875-00-9 N-(N^α-benzyloxycarbonyl-N^α-methyl-O-benzyltyrosyl-N^g-tosylarginyl)bis(4-methylphenyl)methanamine 
• 205874-98-2 N¹-benzyloxycarbonyl-N²-(N^α-benzyloxycarbonyl-N^α-methyl-O-benzyltyrosyl-N^g-tosylarginyl)-1,2-ethanediamine 
• 205874-99-3 N-(N^α-benzyloxycarbonyl-N^α-methyl-O-benzyltyrosyl-N^g-tosylarginyl)ethanamine 
• 95015-70-6 Z-(Me)Tyr(Bzl)-(Me)Ava-(Me)PHA 

Relevant academic research and scientific papers

A simple and rapid protocol for N-methyl-α-amino acids

A two step strategy for optically pure N-Protected-N-methyl-α-amino acids starting from N-protected-α-amino acids via reductive cleavage of oxazolidinones using NaCNBH3/TMSCl is described.

Design and synthesis of peptides passing through the blood-brain barrier

The blood-brain barrier (BBB) is a highly selective membranous barrier regulating the transport of substances in blood into the brain parenchyma. At present, delivery of biologically active peptides or peptide drugs into the brain is quite an important subject from the standpoint of chemotherapy for brain diseases H-MeTyr-Arg-MeArg-D-Leu-NH(CH2)8NH2 termed 001-C8 was first synthesized to elucidate the structural specificity of peptides for passing through the BBB. The Na-methylamino acid and D-amino acid residues were appropriately situated in this peptide to protect against the digestion by peptidase. Furthermore, a number of basic peptides were prepared as 001-C8 analogs for studying the relationship between structure and BBB permeability of peptides.

Intestinal absorption of fluorescence-derivatized cationic peptide 001-C8-NBD via adsorptive-mediated transcytosis

The intestinal absorption of an intact oligopeptide was investigated in rats using a synthetic cationic peptide, 001-C8 (H-MeTyr-Arg-MeArg-d-Leu-NH(CH2)8NH2). The peptide was coupled with 4-nitrobenzo-2-oxa-1,3-diazole (NBD) to prepare a fluorescence-labeled derivative 001-C8-NBD (H-MeTyr-Arg-MeArg-d-Leu-NH(CH2)8NH-NBD) for the purpose of quantification. The degradation half-life of 001-C8-NBD in jejunal homogenate (1mg/mL) was 99.5min, which was significantly longer than that of natural leucine enkephalin (1.14min). The absorption of 001-C8-NBD was evaluated by the vascular-perfusion method. Intact 001-C8-NBD appeared in the blood time-dependently and the absorption volume at 30min (2.75 ± 0.14μL/cm intestine) was significantly larger than that of [3H]PEG 900 (0.88 ± 0.13μL/cm intestine), of which membrane permeability is very low. The absorption of 001-C8-NBD was greatly reduced by an adsorptive-mediated endocytosis inhibitor, protamine (10mM). No inhibition of the absorption of [3H]PEG 900 by protamine was observed. The intestinal absorption was also measured by an in vivo loop method. The absorption clearance of 001-C8-NBD measured by this method (0.083 ± 0.008μL/min/cm intestine) was comparable to that obtained by the vascular perfusion method (0.092 ± 0.005μL/min/cm intestine). All of these data suggested that 001-C8-NBD was absorbed as the intact oligopeptide in the intestine in vivo. Adsorptive-mediated transcytosis is suggested to have enormous potential as an oral delivery system for peptide and/or protein drugs. Copyright (C) 1998 Elsevier Science Ltd.

Analgesic and/or opiate antagonist tripeptide amides and processes for preparation and compositions thereof

A genus of tripeptide amides and fifteen species thereof of Examples 4-18, which are useful as analgesics and/or opiate antagonists, three processes for preparation thereof, pharmaceutical compositions thereof, and the three tripeptide amide species of Examples 1-3, which are not within the genus and are useful as analgesics and/or opiate antagonists, are disclosed.

Analgesic dipeptide amides and method of use and compositions thereof

A genus of dipeptide amides including as the preferred subgenus the dipeptide amides having the structural formula R1 TyrR2 D-AlaNHR4 wherein R1 and R2 are each hydrogen or alkyl provided that at least one of them is other than hydrogen and R4 is phenylalkyl or substituted-phenylalkyl are prepared by condensing the dipeptide with the amine or the amino acid with the amino acid amide and are useful as analgesics.