1168-87-2

Usage

Uses

Used in Pharmaceutical Industry:
Z-ALA-ONP is used as an intermediate in the synthesis of aza peptides for its role in inhibiting and titrating the active sites of cysteine proteinases. These aza peptides have potential applications in the development of drugs targeting various diseases and conditions where cysteine proteinases play a significant role, such as cancer, inflammatory disorders, and parasitic infections.

InChI:InChI=1/C17H16N2O6/c1-12(18-17(21)24-11-13-5-3-2-4-6-13)16(20)25-15-9-7-14(8-10-15)19(22)23/h2-10,12H,11H2,1H3,(H,18,21)/t12-/m0/s1

Upstream product

• 23485-35-0 tris(p-nitrophenyl)-phosphite 
• 1142-20-7 N-Cbz-Ala 
• 100-02-7 4-nitro-phenol 
• 501-53-1 benzyl chloroformate 
• 13795-24-9 benzyl 4-nitrophenyl carbonate 
• 16480-55-0 sodium L-alaninate 

Downstream Products

• 5673-65-4 L-alanine p-nitrophenyl ester hydrobromide 
• 2488-22-4 (S)-tert-butyl 2-((S)-2-(((benzyloxy)carbonyl)amino)propanamido)propanoate 
• 19542-34-8 N-(benzyloxycarbonyl)-L-alanyl-L-serine methyl ester 
• 52895-36-0 Z-L-Ala-L-Val-OEt 
• 5009-52-9 2-(N-Benzyloxycarbonyl-L-alanyl)-hydrazinoessigsaeure 
• 61280-93-1 N^α-Benzyloxycarbonyl-L-alanyl-L-alaninethanolamid 
• 61280-89-5 N^α-Benzyloxycarbonyl-L-alanyl-L-alaninmethylamid 
• 61280-94-2 N^α-Benzyloxycarbonyl-L-alanyl-D-alaninethanolamid 
• 27283-10-9 5-[(N-benzyloxycarbonyl-L-alanyl)-amino]-3-morpholin-4-yl-[1,2,3]oxadiazolium betaine 
• 2682-71-5 [(2S,3S)-2-((S)-2-Benzyloxycarbonylamino-propionylamino)-3-methyl-pentanoylamino]-acetic acid ethyl ester 
• 61280-90-8 N^α-Benzyloxycarbonyl-L-alanyl-D-alaninmethylamid 
• 10087-59-9 Z-Ala-Arg(NO₂)-ONB 
• 4816-92-6 N-(N-Benzyloxycarbonyl-L-alanyl)-glycin-(glykolsaeureamid-ester) 
• 58848-62-7 Boc-L-alanine-p-nitrophenyl ester 

Relevant academic research and scientific papers

Catalyst-Free Insertion of Sulfoxonium Ylides into Aryl Thiols. A Direct Preparation of β-Keto Thioethers

Insertion of sulfoxonium ylides into the S-H bond of aryl thiols without the need for a catalyst is demonstrated, furnishing β-keto thioethers in excellent yield in most cases. The method overcomes traditional syntheses that employ metal catalysts in combination with diazo compounds or toxic and hard-prepared haloketones. The experimental setup consists of mixing the reagents in acetonitrile at room temperature. Additional experimental as well as kinetic isotopic effect studies give some insight into the mechanism of this reaction.

COMPOUNDS AND METHODS FOR DELIVERY OF PROSTACYCLIN ANALOGS

This invention pertains generally to prostacyclin formulations and methods for their use in promoting vasodilation, inhibiting platelet aggregation and thrombus formation, stimulating thrombolysis, inhibiting cell proliferation (including vascular remodeling), providing cytoprotection, preventing atherogenesis and inducing angiogenesis.

Long-lived charge-separated species observed on flash photolysis of peptide conjugates. Interplay of local and radical ion pair triplet states

Peptides composed of alanine (Ala) and tryptophan (Trp), modified with the (nitro)pyrenesulfonyl chromophore (Pyr and NPyr) at the N-terminus have been examined by nanosecond laser flash photolysis. A common phototransient for Pyr-AlaOEt and Pyr-Ala-TrpOEt was observed that exhibited broad absorption at 410-550 nm and decay time constants in the range, τ(1/2) = 20- 40 μs. This species was assigned to the triplet excited state that is local to the pyrene chromophore (3Pyr). For the conjugates having a stronger electron acceptor group at the N-terminus, NPyrAla-TrpOEt and NPyr-Ala-Ala- TrpOEt, the local triplet was replaced with a phototransient whose principal feature is a sharp band at 440 nm (assigned to the NPyr-. radical anion). The radical ion transients for the NPyr peptide derivatives were assigned to intermediates that result from the intramolecular electron transfer quenching of NP excited species by pendant groups (i.e., the indole ring of tryptophan). The lifetimes observed for the radical ion transients associated with the NPyr series were relatively long (extending to ca. 400 ns) and depended in an interesting way on the structure of the peptide linkage. A mechanism of electron transfer in the singlet manifold and recombination yielding a local Pyr triplet state is important for the Pyr series.

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.

Thermodynamic and (1)H NMR Study of Proton Complex Formation of Histidine-containing Cyclodipeptides in Aqueous Solution

A thermodynamic and (1)H NMR study of proton complex formation in aqueous solution of some L-histidine-containing cyclic L-dipeptides has been carried out.The enthalpic and entropic changes associated with protonation of the cyclodipeptides, obtained by potentiometric and calorimetric measurements, together with the (1)H NMR data and NOESY experiments, enable the role played by non-covalent interactions in proton complex formation to be assessed.In addition, a comparison with c(Gly-His) permits the influence of side-chain residues on the conformation of protonated species to be observed.

Dichlorotris(dimethylamino)phosphorane as Dehydration Reagent for the Preparation of Activated (-ONp, -OPcp, -NSu)Esters of N-Protected Multifunctional Amino Acids

Dichlorotris(dimethylamino)phosphorane (5) is an excellent reagent for the preparation of the activated esters of N-protected amino acids 7-9.Besides 4-nitrophenyl-, pentachlorophenyl-, and N-hydroxysuccinimide esters of various N-protected amino acids, in the presence of HOBt benzyloxycarbonyl-threonine N-hydroxysuccinimide ester was obtained for the first time.