70035-45-9

Basic information

• Product Name: L-Methionine, N-[N-[N-[N-[(1,1-dimethylethoxy)carbonyl]glycyl]glycyl]-L-phenylalanyl]-, methyl ester
• CAS NO: 70035-45-9
• Molecular Formula: C24H36N4O7S
• Molecular Weight: 524.638
• Mol File: 70035-45-9.mol

Chemical Properties

• CAS DataBase Reference: L-Methionine, N-[N-[N-[N-[(1,1-dimethylethoxy)carbonyl]glycyl]glycyl]-L-phenylalanyl]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Methionine, N-[N-[N-[N-[(1,1-dimethylethoxy)carbonyl]glycyl]glycyl]-L-phenylalanyl]-, methyl ester(70035-45-9)
• EPA Substance Registry System: L-Methionine, N-[N-[N-[N-[(1,1-dimethylethoxy)carbonyl]glycyl]glycyl]-L-phenylalanyl]-, methyl ester(70035-45-9)

Safety Data

• Hazardous Substances Data: 70035-45-9(Hazardous Substances Data)

Upstream product

• 4530-20-5 BOC-glycine 
• 78553-40-9 glycylphenylalanylmethionine methyl ester hydrochloride 
• 40290-65-1 hydrochloride of methyl ester of L-phenylalanyl-L-methionine 
• 81638-93-9 O-(N-t-butyloxycarbonylglycylglycyl)-2-pyridylmethylketoxime 
• 53487-98-2 N-tert-butoxycarbonyl glycyl glycine methyl ester 
• 63-68-3 L-methionine 
• 31972-52-8 Boc-Gly-Gly-OH 
• 2491-18-1 (S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride 
• 69872-63-5 N-(tert-butyloxycarbonyl)glycyl-L-phenylalanyl-L-methionine methyl ester 
• 81638-94-0 O-(t-butyloxycarbonyl-L-phenylalanyl)-2-pyridylmethylketoxime 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 66866-43-1 N-(t-butoxycarbonyl)glycyl i-butyl carbonate 
• 67729-36-6 Boc-Phe-O-COO-isoBu 
• 40290-63-9 Methyl ester of N-t-butyloxycarbonyl-L-phenylalanyl-L-methionine 

Downstream Products

• 62530-43-2 Boc-Tyr(tert.-Bu)-Gly-Gly-Phe-Met 
• 71921-23-8 Boc-Tyr(tert.-Bu)-Gly-Gly-Phe-Met-OMe 
• 97800-86-7 O-tert-Butyl-N,N-dimethyl-L-tyrosyl-glycyl-glycyl-L-phenylalanyl-L-methionin-methylester 
• 97800-57-2 Me₂Tyr(tBu)-Gly-Gly-Phe-L-Met-NH₂ 
• 97800-59-4 Me₂Tyr-Gly-Gly-Phe-L-Met-NH₂ 
• 73337-50-5 Boc-Gly-Gly-Phe-Met-Thr-Ser-Glu(OtBu)-Lys(Boc)-OH 
• 61370-88-5 [des-tyr¹]-methionine enkephalin 
• 81649-52-7 methyl ester of N,O-di-t-butyloxycarbonyl-L-tyrosylglycylglycyl-L-phenylalanyl-L-methionine 
• 58569-55-4 met-enkephalin 
• 60566-44-1 methyl N-tert-butoxycarbonyl-L-tyrosyldiglycyl-L-phenylalanyl-L-methioninate 
• 59481-77-5 boc-Tyr-Gly-Gly-Phe-Met-OH 
• 70035-46-0 hydrochloride of methyl ester of glycylglycyl-L-phenylalanyl-L-methionine 
• 68800-26-0 N-tert-butoxycarbonylglycylglycylphenylalanylmethionine 
• 68709-93-3 H-Gly-Gly-Phe-Met-OMe 

Relevant articles and documents

Dynamic Kinetic Cross-Electrophile Arylation of Benzyl Alcohols by Nickel Catalysis

Catalytic transformation of alcohols via metal-catalyzed cross-coupling reactions is very important, but it typically relies on a multistep procedure. We here report a dynamic kinetic cross-coupling approach for the direct functionalization of alcohols. The feasibility of this strategy is demonstrated by a nickel-catalyzed cross-electrophile arylation reaction of benzyl alcohols with (hetero)aryl electrophiles. The reaction proceeds with a broad substrate scope of both coupling partners. The electron-rich, electron-poor, and ortho-/meta-/para-substituted (hetero)aryl electrophiles (e.g., Ar-OTf, Ar-I, Ar-Br, and inert Ar-Cl) all coupled well. Most of the functionalities, including aldehyde, ketone, amide, ester, nitrile, sulfone, furan, thiophene, benzothiophene, pyridine, quinolone, Ar-SiMe3, Ar-Bpin, and Ar-SnBu3, were tolerated. The dynamic nature of this method enables the direct arylation of benzylic alcohol in the presence of various nucleophilic groups, including nonactivated primary/secondary/tertiary alcohols, phenols, and free indoles. It thus offers a robust alternative to existing methods for the precise construction of diarylmethanes. The synthetic utility of the method was demonstrated by a concise synthesis of biologically active molecules and by its application to peptide modification and conjugation. Preliminary mechanistic studies revealed that the reaction of in situ formed benzyl oxalates with nickel, possibly via a radical process, is an initial step in the reaction with aryl electrophiles.

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.

Selectivity in the Trimethylsilylation and Acylation of Peptide Bonds, and its Application to Modification of the Enkephalins

N.m.r. spectra of N-acylated peptides, formed by reaction of protected peptides with silylating agents followed by acylation, have provided a means for assessing selectivity in the acylation of amide bonds.Amino-acids such as valine and phenylalanine prev

A Convenient Synthesis of Met-enkephalin Using 1-β-Naphthalenesulphonyloxybenzotriazole for Peptide Bond Formation

A convenient procedure for the synthesis of Met-enkephalin involving the use of 1-β-naphthalenesulphonyloxybenzotriazole as the peptide coupling reagent is described.Boc group is employed for the protection of α-NH2 functions of amino acids and its cleavage from the intermediate peptides is brought about by HCOOH in the presence of C6H5-OCH3 and SH-(CH2)2-SH without the formation of side products.The resulting formates are converted to the corresponding hydrochlorides prior to their coupling with the carboxy component.All the intermediate peptides have been obtained in high yields.

O-(N-ACYLAMINOACYL)-2-PYRIDYLMETHYLKETOXIMES AND THEIR USE IN PEPTIDE SYNTHESIS

Preparation of Leu-enkephalin, Met-enkephalin and one analog of Leu-enkephalin by using O-(N-acylaminoacyl)-2-pyridylketoximes is described.Both the side products and the unreacted active amino acid derivatives were removed by utilizing the formation of a copper complex with 2-pyridylmethylketoxime.