2754-02-1

Upstream product

• 4070-48-8 L-Valine methyl ester 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 6306-52-1 L-valine methylester hydrochloride 
• 81000-39-7 (S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanethioic S-acid 
• 4070-48-8 L-valine methyl ester 
• 17498-50-9 L-valine hydrochloride 
• 93605-47-1 (S)-methyl 2-(1H-imidazole-1-carboxamido)-3-methylbutanoate 
• 1446274-23-2 (S)-Se-((9H-fluorenyl)methyl) 2-((tert-butoxycarbonyl)amino)-3-phenylpropaneselenoate 
• 63-91-2 L-phenylalanine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 72-18-4 L-valine 
• 33857-75-9 N-tert-butoxycarbonyl-L-phenylalanine 2-pyridyl thiol ester 

Downstream Products

• 80870-38-8 (S)-methyl 2-((S)-2-amino-3-phenylpropanamido)-3-methylbutanoate 
• 735200-29-0 L-Phe-L-Val-NH-NH-Z 
• 5196-44-1 tert.-Butyloxycarbonyl-L-Phe-L-Val-NH-NH-Z 
• 35590-86-4 (3S,6S)-3-(1-methylethyl)-6-(phenylmethyl)piperazine-2,5-dione 
• 5196-43-0 tert-butyl ((S)-1-(((S)-1-hydrazinyl-3-methyl-1-oxobutan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate 
• 1447815-54-4 L-isoseryl-L-phenylalanyl-L-valine 

Relevant academic research and scientific papers

Phenysilane and Silicon Tetraacetate: Versatile Promotors for Amide Synthesis

Phenylsilane was reevaluated as a useful coupling reagent for amide synthesis. At room temperature, a wide range of amides and peptides were obtained in good to excellent yields (up to 99 %). For the first time, Weinreb amides synthesis mediated by a hydrosilane were also documented. Comparative experiments with various acetoxysilanes suggested the involvement of a phenyl-triacyloxysilane. From this mechanistic study, silicon tetraacetate was shown as an efficient amine acylating agent.

Photoredox-Mediated Reaction of gem-Diborylalkenes: Reactivity Toward Diverse 1,1-Bisborylalkanes

The use of gem-diborylalkenes as radical-reactive groups is explored for the first time. These reactions provide an efficient and general method for the photochemical conversion of gem-diborylalkenes to rapidly access 1,1-bisborylalkanes. This method expl

Synthesis and biological evaluation of a novel series of curcumin-peptide derivatives as PepT1-mediated transport drugs

Curcumin (CUR) is a natural yellow pigment from turmeric with extensive bioactivities. However its relatively poor solubility limited its absorption and bioavailability. In this study, a novel series of CUR-peptide conjugates were designed and synthesized

TCFH-NMI: Direct Access to N-Acyl Imidazoliums for Challenging Amide Bond Formations

Challenging couplings of hindered carboxylic acids with non-nucleophilic amines to form amide bonds can be accomplished in high yields, and in many cases, with complete retention of the adjacent stereogenic centers using the combination of N,N,N′,N′-tetramethylchloroformamidinium hexafluorophosphate (TCFH) and N-methylimidazole (NMI). This method allows for in situ generation of highly reactive acyl imidazolium ions, which have been demonstrated to be intermediates in the reaction. The reagent delivers high reactivity similar to acid chlorides with the ease of use of modern uronium reagents.

Sequential One-Pot Synthesis of Dipeptides through the Transient Formation of CDI-N-Protected α-Aminoesters

The synthesis of dipeptides through a sequential one-pot procedure from commercially available protected amino acids is described. The transformation relies on the use of in situ generated transiently CDI-protected α-amino esters (CDI, e.g. N,N′-carbonyldiimidazole). In addition of being a highly atom-economical process, the couplings take place under very mild and neutral conditions without adding a base to the reaction medium. This protocol provides a concise and less costly route to dipeptide derivatives (12 examples, up to 87% yield) and is compatible with commonly used N-urethane protecting groups. Moreover, no epimerization was detected even when sensitive Boc-Cys(Bn)?OH was used. (Figure presented.).

Marine natural occurring 2,5-diketopiperazines: Isolation, synthesis and optical properties

Seven 2,5-diketopiperazines (DKPs) were isolated from the Fijian marine sponge Acanthella cavernosa. NMR and circular dichroism (CD) comparison with synthetic L-L DKPs allowed us to determine unambiguously the L-L absolute configuration of the natural DKPs. This work initiated the setting up of an optical properties database of natural DKPs, including specific rotation and CD.

Borinic acid catalysed peptide synthesis

The catalytic synthesis of peptides is a major challenge in the modern organic chemistry hindered by the well-established use of stoichiometric coupling reagents. Herein, we describe for the first time that borinic acid is able to catalyse this reaction under mild conditions with an improved activity compared to our recently developed thiophene-based boronic acid. This catalyst is particularly efficient for peptide bond synthesis affording dipeptides in good yields without detectable racemization.

Catalytic chemical amide synthesis at room temperature: One more step toward peptide synthesis

An efficient method has been developed for direct amide bond synthesis between carboxylic acids and amines via (2-(thiophen-2-ylmethyl)phenyl)boronic acid as a highly active bench-stable catalyst. This catalyst was found to be very effective at room temperature for a large range of substrates with slightly higher temperatures required for challenging ones. This methodology can be applied to aliphatic, α-hydroxyl, aromatic, and heteroaromatic acids as well as primary, secondary, heterocyclic, and even functionalized amines. Notably, N-Boc-protected amino acids were successfully coupled in good yields with very little racemization. An example of catalytic dipeptide synthesis is reported.

Highly stereoselective synthesis of natural-product-like hybrids by an organocatalytic/multicomponent reaction sequence

In an endeavor to provide an efficient route to natural product hybrids, described herein is an efficient, highly stereoselective, one-pot process comprising an organocatalytic conjugate addition of 1,3-dicarbonyls to α,β-unsaturated aldehydes followed by

Iodine-Mediated Oxidative Coupling of Hydroxamic Acids with Amines towards a New Peptide-Bond Formation

An efficient and straightforward approach for the coupling of Nα-protected hydroxamic acids with an amino component in the presence of iodine is delineated. The reaction is mediated by the formation of unstable but reactive acyl nitroso intermediates. The peptide hydroxamic acids were found to be useful substrates in coupling reactions.