42166-73-4

Upstream product

• 4132-86-9 N-benzyloxycarbonylalanine 
• 62-53-3 aniline 
• 13139-27-0 L-α-N-Cbz-alaninamide 
• 10068-54-9 bis(N-benzyloxycarbonyl-L-alanyl)oxide 
• 1142-20-7 N-Cbz-Ala 
• 3401-36-3 (N-benzyloxycarbonyl)-L-alanine N-hydroxysuccinimide ester 
• 543-27-1 isobutyl chloroformate 
• 28819-05-8 (S)-2-benzyloxycarbonylamino-propionic acid methyl ester 

Downstream Products

• 60756-56-1 (S)-2-amino-N-phenylpropanamide 
• 871579-19-0 (Z)-2-acetylamino-N-[(S)-N-phenyl-2-propionamido]-3-(1-naphthyl)-2-propenamide 

Relevant academic research and scientific papers

Visible Light-Induced Amide Bond Formation

A metal-, base-, and additive-free amide bond formation reaction was developed under an organic photoredox catalyst. This green approach showed excellent functional selectivity without affecting other functional groups such as alcohols, phenols, ethers, esters, halogens, or heterocycles. This method featured a broad substrate scope, good compatibility with water and air, and high yields (≤95%). The potential utilities were demonstrated by the synthesis of important drug molecules such as paracetamol, melatonin, moclobemide, and acetazolamide.

General and scalable amide bond formation with epimerization-prone substrates using T3P and pyridine

The mild combination of T3P (n-propanephosphonic acid anhydride) and pyridine has been developed for low-epimerization amide bond formation and implemented for the synthesis of a key intermediate to a glucokinase activator. This robust method is general for the coupling of various racemization-prone acid substrates and amines, including relatively non-nucleophilic anilines, and provides amides in high yields with very low epimerization. With easy reaction setup and product isolation, this protocol offers several practical and experimental benefits.

Enzymatic synthesis of C-terminal arylamides of amino acids and peptides

(Chemical Equation Presented) A mild and cost-efficient chemo-enzymatic method for the synthesis of C-terminal arylamides of amino acid and peptides is described. Using the industrial serine protease Alcalase under near-anhydrous conditions, C-terminal arylamides of N-Cbz-protected amino acids and peptides could be obtained from the corresponding C-terminal carboxylic acids, methyl (Me) or benzyl (Bn) esters, in high chemical and enantio- and diastereomeric purities. Yields ranged between 50% and 95% depending on the size of the aryl substituents and the presence of electron-withdrawing substituents. Complete α-C-terminal selectivity could be obtained even in the presence of various unprotected side-chain functionalities such as β/γ-carboxyl, hydroxyl, and guanidino groups. In addition, the use of the cysteine protease papain and the lipase Cal-B gave anilides in high yields. The chemo-enzymatic synthesis of arylamides proved to be completely free of racemization, in contrast to the state-of-the-art chemical methods.

Enantioselective nickel-catalyzed conjugate addition of dialkylzinc to chalcones using chiral α-amino amides

A series of α-amino amides derived from natural amino acids (alanine, valine, phenylalanine, isoleucine, and phenylglycine) have been synthesized and fully characterized. Their Ni(II) complexes prepared from Ni(acac)2 catalyze the enantioselective conjugate addition of diethylzinc to chalcones in high yields and in good enantioselectivities (up to 84%). The side chain of the amino acid and the substituents in the amide nitrogen govern the enantioselectivity of the catalytic process.

Electron transfer-initiated asymmetric photocyclization of chiral auxiliary-substituted N-acyl-α-dehydro(1-naphthyl)alaninamides to the corresponding 3,4-dihydrobenzo[f]quinolinone derivatives

Photoinduced electron transfer reactions of the title N-acyl-α- dehydronaphthylalaninamides [(Z)-1] with (S)-1-phenylethylamino and (S)-alaninamide auxiliary groups in methanol containing a tertiary amine were shown to form (R,S)- and (S,S)-3,4-dihydroben

A novel generation of coupling reagents. Enantiodifferentiating coupling reagents prepared in situ from 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) and chiral tertiary amines

Coupling of racemic N-protected amino acids with amino components by means of 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) in the presence of chiral tertiary amines such as strychnine, brucine, and sparteine proceeds enantioselectively, affording appropriate amides or dipeptides in 69-85% yield. The configuration of the preferred enantiomer and enantiomeric enrichment depend on the structures of the amine and carboxylic acid. Calculated Kagan enantioselectivity parameters (s) are in the range 1.6-195. Chiral triazinylammonium chlorides formed in situ from CDMT and chiral tertiary amines are postulated as reactive intermediates involved in the process of enantioselective activation of N-protected amino acids.

Coordination compounds of tripeptides and pentapeptides containing L-histidyl residues. Studies towards structural modes for the active site of copper proteins

Five small, completely protected, L-histidyl(NτBzl)-containing peptides, were synthesized and characterized by NMR spectroscopy, i.e., R-Ala-His(Nτ-Bzl)-Ala-R' (1), R-His(Nτ-Bzl)-Ala-Ala-Ala-Met-R' (2), R-His(Nτ-Bzl)-Ala-Ala-Ala-His(Nτ-Bzl)-R' (3), R-His(Nτ-Bzl)-Ala-His(Nτ-Bzl)-Ala-His(Nτ-Bzl)-R' (4), R-His(Nτ-Bzl)-Ala-His(Nτ-Bzl)-R' (5), in which: R is phenylacetyl (PhCH2CO-, R' is phenylamino (-NHPh); Bzl is benzyl (PhCH2-).It has been shown that benzylation of histidine residues takes place at the Nτ atom of the imidazole.The resulting peptide derivatives appear to be good ligands for CoII, ZnII and CuI.Titrations of zinc chloride solutions towards peptide solutions (in dmso-d6, dimethyl sulfoxide followed by NMR spectroscopy show the formation of the two species ?His)2Cl2> and ?His)(dmso)Cl2>.Copper(I)-chloride titrations result in formation of trigonal planar and tetrahedral complexes (in dmso-d6).Zinc, copper and cobalt trifluoromethanesulfonates were also investigated, and corresponding tetrahedral species with additional dmso ligands replacing chloride were obtained.In addition, octahedral complexes have been found, as shown for cobalt(II) using ligand-field spectroscopy.Conductivity experiments of zinc chloride complexes in dmso and chloroform indicate non-electrolytes.Their very low conductivity in methanol indicates only slight dissociation of chloride, in agreement with a tetrahedral geometry for zinc(II).For ?His)2Cl2>, the UV-VIS adsorption spectra in dmso and in the solid state (diffuse reflection) are comparable, indicating tetrahedral geometry, with a CoN2Cl2 chromophore.

PAPAIN-CATALYZED SYNTHESIS OF 2-NAPHTHYLAMIDES OF N-ACYLAMINO ACIDS AND DIPEPTIDES

2-Naphthylamides of several N-acylamino acids were prepared by papain-catalyzed condensation reaction in acidic medium.Under the same conditions, papain catalyzed the synthesis of peptide bond between benzyloxycarbonylglycine and phenylalanine 2-naphthyla

DIPEPTIDE DERIVATIVES

The present disclosure relates to dipeptide derivatives. These novel compounds are useful as elastase inhibitors.