59481-77-5

Upstream product

• 134532-09-5 BocTyr(2-BrZ)GlyGlyPheMetOH 
• 58569-55-4 met-enkephalin 
• 41840-28-2 S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine 
• 7535-56-0 p-nitrophenylester of N-tert-butoxycarbonylphenylalanine 
• 63-68-3 L-methionine 
• 68800-26-0 N-tert-butoxycarbonylglycylglycylphenylalanylmethionine 
• 62530-45-4 (S)-2-((S)-2-Amino-3-phenyl-propionylamino)-4-methylsulfanyl-butyric acid; hydrochloride 
• 61543-56-4 boc-Phe-Met-OH 
• 47689-67-8 (S)-3-[4-(2-Bromo-benzyloxycarbonyloxy)-phenyl]-2-tert-butoxycarbonylamino-propionic acid 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 2488-15-5 N-tert-butoxycarbonyl-L-methionine 
• 70035-46-0 hydrochloride of methyl ester of glycylglycyl-L-phenylalanyl-L-methionine 
• 67729-36-6 Boc-Phe-O-COO-isoBu 
• 70035-45-9 N-tert-Butyloxycarbonyl-glycyl-glycyl-L-phenylalanyl-L-methionin-methylester 

Downstream Products

• 58569-55-4 met-enkephalin 

Relevant academic research and scientific papers

Convenient high yielding gram scale solution synthesis of methionine-enkephalin

A simple, large-scale synthesis of a cytokine, methionine-enkephalin, Tyr-Gly-Gly-Phe-Met, has been elaborated. Classical solution peptide chemistry methods without protection of amino acid side-chain functions and l+(2+2) segment condensation were used. A nine-step synthesis from commercial amino acid derivatives was developed with yields ranging from 86% to 99%, averaging 92%. The purity of all intermediates was found to be 99.0-100% by HPLC. The process has been used to prepare greater than 150 g quantities of the pentapeptide as a monohydrate of 100% purity. Hydantoin formation was observed during saponification of Boc-TyrGly-Gly-Phe-Met-OMe and minimised.

The use of p-toluenesulfonic acid for removal of the N-T-butoxy-carbonyl protecting group in solid phase peptide synthesis

The usefulness of p-toluenesulfonic acid in THF/CH2Cl2 for Boc removal in solid phase peptide synthesis has been demonstrated through the syntheses of Leu-5 and Met-5 enkephalin acids.

SYNTHESIS OF ENKEPHALINS BY THE METHOD OF POLYMERIC ACTIVATED ESTERS BASED ON 4-HYDROXY-3-NITROBENZOPHENONE

Leucine- and methionine-enkephalins have been synthesized by the successive growth of the peptide chain from the C-end by the method of polymeric activated esters based on 4-hydroxy-3-nitrobenzophenone with yields of 90 and 70percent, respectively, calculated on the initial C-terminal amino acid.Polystyrene with 2percent of divinylbenzene was used as the polymeric matrix.Using the synthesis of methionine-enkephalin as an example, the possibility has been shown of using polymeric activated esters for the synthesis of peptides with a free carboxy group.

ON THE USE OF CARBOXAMIDOMETHYL ESTERS ( CAM ESTERS ) IN THE SYNTHESIS OF MODEL PEPTIDES. SCOPE AND LIMITATIONS

The usefulness of carboxamidomethyl esters ( CAM esters ) as a carboxyl protecting group for peptide synthesis was demonstrated.The synthesis of the chemotactic peptide For-Met-Leu-Phe-OH as well as the synthesis of Met-enkephalin using CAM ester as carbo

Polypeptide and its production and use

Novel polypeptide of the formula: H-Tyr-Gly-Gly-Phe-Met-Lys-Pro-Tyr-Thr-Lys-Gln-Ser-His-Lys-Pro-Leu-Ile-Thr-Leu-Leu-Lys-His-Ile-Thr-Leu-Lys-Asn-Glu-Gln-OH is useful as an analgesic agent. Methods of its preparation are also disclosed.

New Protective Groups for Peptide Synthesis. 4. Chromone-Derived Protection for Amine and Carboxyl Functions

A new urethane-type protective group for amines, the 2-(trifluoromethyl)-6-chromonylmethylenecarbonyl (Tcroc)group (15), and a new benzyl ester type protective group for carboxylic acids, the 2-(trifluoromethyl)-6-chromonylmethylene (Tcrom) group (12), are described.The Tcroc and Tcrom groups are shown to be rapidly cleaved by neat propylamine or dilute ethanolic hydrazine and to resist cleavage by ethyl alaninate and a variety of acidic reagents.Independent removal of Tcroc or Tcrom and of Boc or tert-butyl ester groups, each in the presence of the other, is demonstrated by a synthesis of Nα-Boc methionine enkephalin.