149296-96-8

Basic information

• Product Name: N-fmoc-OtBu-L-tyrosinyl-L-alanine methyl ester
• Synonyms: N-fmoc-OtBu-L-tyrosinyl-L-alanine methyl ester
• CAS NO: 149296-96-8
• Molecular Weight: 544.648
• Mol File: 149296-96-8.mol

Chemical Properties

• CAS DataBase Reference: N-fmoc-OtBu-L-tyrosinyl-L-alanine methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-fmoc-OtBu-L-tyrosinyl-L-alanine methyl ester(149296-96-8)
• EPA Substance Registry System: N-fmoc-OtBu-L-tyrosinyl-L-alanine methyl ester(149296-96-8)

Safety Data

• Hazardous Substances Data: 149296-96-8(Hazardous Substances Data)

Upstream product

• 2491-20-5 L-alanine methyl ester hydrochloride 
• 71989-38-3 Fmoc-Tyr(tBu)-OH 
• 10065-72-2 L-Alanine methyl ester 
• 1436573-85-1 N-fmoc-O-tBu-L-tyrosinyl-N-methyl-4-nitrobenzenesulfonamide 

Downstream Products

• 149296-97-9 Fmoc-Tyr-Ala-OMe 

Relevant articles and documents

An efficient mechanochemical synthesis of amides and dipeptides using 2,4,6-trichloro-1,3,5-triazine and PPh3

A rapid, facile, and efficient mechanochemical synthesis of amides from carboxylic acids has been developed through an in situ acid activation with 2,4,6-trichloro-1,3,5-triazine and a catalytic amount of PPh3. Under room temperature solvent-drop grinding of the reactants in the presence of an inorganic base, a variety of carboxylic acids including aromatic acids, aliphatic acids, and N-protected α-amino acids undergo amidation to afford amides in moderate to excellent yields. The method is also compatible with Fmoc, Cbz, and Boc protecting groups which yields protected optically active dipeptides without detectable racemization.

C → N and N → C solution phase peptide synthesis using the N-acyl 4-nitrobenzenesulfonamide as protection of the carboxylic function

In this paper we describe a solution phase peptide synthesis strategy using the 4-nitrobenzenesulfonamido/N-methyl-4-nitrobenzenesulfonamido group as a protecting/activating system of the carboxyl function. The 4- nitrobenzenesulfonamido group is stable during peptide chain elongation (Fmoc chemistry). The N-aminoacyl or N-dipeptidyl-4-nitrobenzensulfonamides, when activated by methylation, can be easily coupled with another amino acid or reconverted into the free-carboxyl function amino acids or peptides. This activatable protecting group allows both the C → N and the N → C direction solution phase peptide synthesis. We also verified that the absolute configuration at the chiral centers does not change during the coupling reactions. This journal is The Royal Society of Chemistry 2013.

Evaluation of the final deprotection system for the solid-phase synthesis of tyr(SO3H)-containing peptides with 9-fluorenylmethyloxycarbonyl (Fmoc)-strategy and its application to the synthesis of cholecystokinin (CCK)-12

Acidolytic deprotection and cleavage conditions for an acid-labile Tyr(SO3H)-containing peptide were systematically examined with respect to acid, temperature, and scavenger. The 90% aqueous trifluoroacetic acid (TFA)-based reagent systems (90%