47091-42-9

Upstream product

• 6456-74-2 Glycine tert-butyl ester 
• 23358-34-1 Z-Phe-Gly-OtBu 
• 35661-40-6 N-Fmoc L-Phe 
• 27532-96-3 glycine tert-butyl ester hydrochloride 
• 63-91-2 L-phenylalanine 
• 3588-57-6 Z-DL-Phe-OH 
• 1161-13-3 N-Cbz-L-Phe 

Downstream Products

• 950584-13-1 tert-butyl (N-allyl-N-trifluoroacetyl-(S)-phenylalanyl)glycinate 

Relevant academic research and scientific papers

Peptide Bond Formation of Amino Acids by Transient Masking with Silylating Reagents

A one-pot peptide bond-forming reaction has been developed using unprotected amino acids and peptides. Two different silylating reagents, HSi[OCH(CF3)2]3 and MTBSTFA, are instrumental for the successful implementation of this approach, being used for the activation and transient masking of unprotected amino acids and peptides at C-termini and N-termini, respectively. Furthermore, CsF and imidazole are used as catalysts, activating HSi[OCH(CF3)2]3 and also accelerating chemoselective silylation. This method is versatile as it tolerates side chains that bear a range of functional groups, while providing up to >99% yields of corresponding peptides without any racemization or polymerization.

Protecting-Group-Free Amidation of Amino Acids using Lewis Acid Catalysts

Amidation of unprotected amino acids has been investigated using a variety of ‘classical“ coupling reagents, stoichiometric or catalytic group(IV) metal salts, and boron Lewis acids. The scope of the reaction was explored through the attempted synthesis of amides derived from twenty natural, and several unnatural, amino acids, as well as a wide selection of primary and secondary amines. The study also examines the synthesis of medicinally relevant compounds, and the scalability of this direct amidation approach. Finally, we provide insight into the chemoselectivity observed in these reactions.

A dithienylethene-based rewritable hydrogelator

Dithienylethene photochromic switching units have been incorporated into a hydrogelating system based on a tripeptide motif. The resulting hybrid system provided both a photochromic response and the ability to gelate water under acidic and neutral conditi

PHOSPHONATED RIFAMYCINS AND USES THEREOF FOR THE PREVENTION AND TREATMENT OF BONE AND JOINT INFECTIONS

The present invention relates to phosphonated Rifamycins, and methods of making and using such compounds. These compounds are useful as antibiotics for prophylaxis and/or the treatment of bone and joint infections, especially for the prophylaxis and/or treatment of osteomyelitis.

Highly stereoselective peptide modifications through Pd-catalyzed allylic alkylations of chelated peptide enolates

Deprotonation of peptides in the presence of zinc chloride gives rise to highly reactive nucleophiles that can be subjected to palladium-catalyzed allylic alkylation reactions. Excellent diastereoselectivities are obtained that are nearly independent of the allylic substrate used. By using this protocol, highly functionalized side chains can also be incorporated in excellent yields and selectivities. The stereochemicaloutcome of the reaction is exclusively controlled by the peptide chain as long as terminal π-allyl-palladium complexes are involved. Probably, there is a threefold coordination, at least, ofthe deprotonated peptide chain to the chelating zinc ion. In such metal peptide complexes, one face of the generated enolate is shielded by the side chain of the adjacent amino acid, thus directing the electrophilic attack onto the opposite face. This behavior explains why an S amino acid always generates an R amino acid (and the other way round).