2280-66-2

Upstream product

• 15761-38-3 L-N-Boc-Ala 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 19460-86-7 (N-methyl)-L-phenylalanine methyl ester hydrochloride 
• 98908-60-2 Boc-Ala-OTAP 
• 66024-53-1 BOC-Ala-POBT 
• 128369-71-1 (S)-methyl-(N-allyloxycarbonyl)phenylalaninate 
• 591-50-4 iodobenzene 
• 170454-76-9 (R)-2-((S)-2-tert-Butoxycarbonylamino-propionylamino)-3-iodo-propionic acid methyl ester 
• 3392-05-0 Boc-Ala-O-N-hydroxysuccinimide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 5872-22-0 N-pivaloylalanine 
• 170454-75-8 (R)-2-((S)-2-tert-Butoxycarbonylamino-propionylamino)-3-chloro-propionic acid methyl ester 
• 631914-55-1 Boc-L-Ala-Cl 

Downstream Products

• 75286-45-2 Boc-Ala-Phe-Leu-NH₂ 
• 2754-00-9 Boc-Ala-Phe-Leu-OH 
• 2421-58-1 Boc-Ala-Phe-Ile-Gly-NH-NH₂ 
• 21853-73-6 Boc-Ala-Phe-Ile-Gly-Leu-Met-NH₂ 
• 40298-89-3 L-alanyl-L-phenylalanine methyl ester 
• 2448-58-0 (S)-2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)-3-phenylpropanoic acid 
• 27220-69-5 Boc-Ala-Phe-NH₂ 
• 2280-75-3 L-alaninyl-L-phenylalanine methyl ester hydrochloride 
• 87892-68-0 methyl L-alanyl-L-phenylalanine trifluoroacetate 
• 126027-99-4 tert-butoxycarbonyl-L-alanylsulfonyl-L-phenylalanine 
• 206123-98-0 (S)-2-[(S)-2-((S)-2-tert-Butoxycarbonylamino-thiopropionylamino)-propionylamino]-3-phenyl-propionic acid methyl ester 
• 82527-18-2 tert-butyl N-((1S)-2-{[(1S)-1-benzyl-2-hydroxyethyl]amino}-1-methyl-2-oxoethyl)carbamate 
• 208255-34-9 (S)-2-{(S)-2-[2-(3,5-Difluoro-phenyl)-acetylamino]-propionylamino}-3-phenyl-propionic acid methyl ester 
• 197505-60-5 (S)-2-[(S)-2-((S)-2-tert-Butoxycarbonylamino-propionylamino)-3-phenyl-propionylamino]-3-hydroxy-propionic acid methyl ester 

Relevant academic research and scientific papers

Controlling Amphiphilic Polymer Folding beyond the Primary Structure with Protein-Mimetic Di(Phenylalanine)

While methods for polymer synthesis have proliferated, their functionality pales in comparison to natural biopolymers-strategies are limited for building the intricate network of noncovalent interactions necessary to elicit complex, protein-like functions

Effect of Stereochemistry on Chirality and Gelation Properties of Supramolecular Self-Assemblies

Although chiral nanostructures have been fabricated at various structural levels, the transfer and amplification of chirality from molecules to supramolecular self-assemblies are still puzzling, especially for heterochiral molecules. Herein, four series o

Synthesis of Dipeptide, Amide, and Ester without Racemization by Oxalyl Chloride and Catalytic Triphenylphosphine Oxide

An efficient triphenylphosphine oxide-catalyzed amidation and esterification for the rapid synthesis of a series of dipeptides, amides, and esters is described. This reaction is applicable to challenging couplings of hindered carboxylic acids with weakly

Chiral Overpass Induction in Dynamic Helical Polymers Bearing Pendant Groups with Two Chiral Centers

The dynamic behavior of helical polymers bearing pendant groups with two chiral centers was studied. Controlled conformational changes at the chiral units placed either closer to or further away from the main chain promote different helical structures. Al

Pd-Catalyzed Site-Selective C(sp2)-H Olefination and Alkynylation of Phenylalanine Residues in Peptides

Pd-catalyzed site-selective C(sp2)-H olefination and alkynylation of phenylalanine residues in peptides are described. The amino acids within the peptides are used as native bidentate directing groups to facilitate C-H functionalization. This p

4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Toluene-4-sulfonate (DMT/NMM/TsO?) Universal Coupling Reagent for Synthesis in Solution

4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium toluene-4-sulfonate (DMT/NMM/TsO?), a representative member of the inexpensive and environmentally-friendly N-triazinylammonium family of sulfonates, has been found to be a very effective coupling reagent for the synthesis of amides, esters and peptides in solution. This study confirms the usefulness of DMT/NMM/TsO? for peptide synthesis in solution, starting from Z-, Fmoc-, and Boc-protected substrates as well as unnatural building blocks. Peptide synthesis with DMT/NMM/TsO? produced high yields, with high crude product purity and low risk of racemization. In all cases, stoichiometric amounts of reagents were used and the standard synthetic procedure, without the need for time-consuming optimization stages or expensive chromatographic purification. DMT/NMM/TsO? was also found to be very useful for the synthesis of oligopeptides using a fragment coupling strategy.

Pd-catalyzed intramolecular C(sp2)-H amination of phenylalanine moieties in dipeptides: Synthesis of indoline-2-carboxylate-containing dipeptides

A palladium-catalyzed intramolecular C(sp2)-H amination of phenylalanine moieties in dipeptides is described. By this protocol, a series of indoline-2-carboxylate-containing dipeptides were synthesized from dipeptides. The N-protected amino aci

Hydrogen bond surrogate stabilized water soluble 310-helix from a disordered pentapeptide containing coded α-amino acids

Replacing a hypothetical i + 3 → i peptide H-bond in a disordered pentapeptide, that lacks any helicogenic Cα-tetrasubstituted residues, with a propyl linker and carbamylating the N-terminal nitrogen constrains it in the elusive 310-helical structure with high helicity and stability under varying conditions of temperature and pH, confirmed by NMR and CD analyses.

Cyclizing pentapeptides: Mechanism and application of dehydrophenylalanine as a traceless turn-inducer

Dehydrophenylalanine is used as a traceless turn-inducer in the total synthesis of dichotomin E. Macrocyclization of the monomer is achieved in high yields and selectivity over cyclodimerization under conditions 100 times more concentrated than previously achieved. The enamide facilitates ring closing, and Rh-catalyzed hydrogenation of the unsaturated cyclic peptide results in selective formation of the natural product or its epimer, depending on our choice of phosphine ligand. NMR analysis and molecular modeling revealed that the linear peptide adopts a left-handed α-turn that preorganizes the N- and C-termini toward macrocyclization.

Diversity of Secondary Structure in Catalytic Peptides with β-Turn-Biased Sequences

X-ray crystallography has been applied to the structural analysis of a series of tetrapeptides that were previously assessed for catalytic activity in an atroposelective bromination reaction. Common to the series is a central Pro-Xaa sequence, where Pro is either l- or d-proline, which was chosen to favor nucleation of canonical β-turn secondary structures. Crystallographic analysis of 35 different peptide sequences revealed a range of conformational states. The observed differences appear not only in cases where the Pro-Xaa loop-region is altered, but also when seemingly subtle alterations to the flanking residues are introduced. In many instances, distinct conformers of the same sequence were observed, either as symmetry-independent molecules within the same unit cell or as polymorphs. Computational studies using DFT provided additional insight into the analysis of solid-state structural features. Select X-ray crystal structures were compared to the corresponding solution structures derived from measured proton chemical shifts, 3J-values, and 1H-1H-NOESY contacts. hese findings imply that the conformational space available to simple peptide-based catalysts is more diverse than precedent might suggest. The direct observation of multiple ground state conformations for peptides of this family, as well as the dynamic processes associated with conformational equilibria, underscore not only the challenge of designing peptide-based catalysts, but also the difficulty in predicting their accessible transition states. These findings implicate the advantages of low-barrier interconversions between conformations of peptide-based catalysts for multistep, enantioselective reactions.