4512-31-6

Upstream product

• 98946-18-0 tert-Butyl 2,2,2-trichloroacetimidate 
• 15030-72-5 Z-Aib-OH 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 501-53-1 benzyl chloroformate 
• 1907-33-1 lithium tert-butoxide 
• 115-11-7 isobutene 

Downstream Products

• 1361051-51-5 Z-Sar-Aib-O(t-Bu) 
• 4512-38-3 Z-(Aib)4-OtBu 
• 1185571-72-5 tert-butyl N-({4-[6-amino-5-(2,4-difluorobenzoyl)-2-oxopyridin-1(2H)-yl]phenyl}acetyl)-2-methylalaninate 
• 1185571-70-3 tert-butyl N-(2-{4-[6-amino-5-(2,4-difluorobenzoyl)-2-oxopyridin-1(2H)-yl]phenyl}ethyl)-2-methylalaninate 
• 845877-33-0 Z-Aib-Gly-Leu-Aib-Ot-Bu 
• 1359857-17-2 Fmoc-Aib-Lys(Z)-Leu-Aib-OtBu 
• 1359857-15-0 Z-Gly-Gly-Leu-Aib-OtBu 
• 845877-32-9 Z-Gly-Leu-Aib-Ot-Bu 
• 669766-81-8 C₂₂H₃₄N₂O₅ 
• 1359857-28-5 Z-Aib-Gly-Leu-Aib-Gly-Gly-Leu-Aib-OtBu 
• 83537-96-6 Benzyloxycarbonyl-L-prolyl-leucyl-α-aminoisobutyryl-α-aminoisobutyric acid tert-butyl ester 
• 84758-65-6 Z-L-Gln-Aib-OtBu 
• 84758-64-5 Z-L-Val-Aib-OtBu 
• 84758-84-9 Z-Ala-Aib-OtBu 

Relevant academic research and scientific papers

Deracemization and the first CD spectrum of a 310-helical peptide made of achiral α-amino-isobutyric acid residues in a chiral membrane mimetic environment

Interaction of the racemic helical homo-octapeptide made by the achiral Cα-methyl alanine (Aib) amino acid with a chiral enantiopure micellar aggregate made of N-dodecylproline led to the deracemization of the helical Aib sequence thus allowing

Toward the selective delivery of chemotherapeutics into tumor cells by targeting peptide transporters: Tailored gold-based anticancer peptidomimetics

Complexes [AuIIIX2(dtc-Sar-AA-O(t-Bu))] (AA = Gly, X = Br (1)/Cl (2); AA = Aib, X = Br (3)/Cl (4); AA = l-Phe, X = Br (5)/Cl (6)) were designed on purpose in order to obtain gold(III)-based anticancer peptidomimetics that might specifically target two peptide transporters (namely, PEPT1 and PEPT2) upregulated in several tumor cells. All the compounds were characterized by means of FT-IR and mono- and multidimensional NMR spectroscopy, and the crystal structure of [AuIIIBr2(dtc-Sar-Aib-O(t- Bu))] (3) was solved and refined. According to in vitro cytotoxicity studies, the Aib-containing complexes 3 and 4 turned out to be the most effective toward all the human tumor cell lines evaluated (PC3, DU145, 2008, C13, and L540), reporting IC50 values much lower than that of cisplatin. Remarkably, they showed no cross-resistance with cisplatin itself and were proved to inhibit tumor cell proliferation by inducing either apoptosis or late apoptosis/necrosis depending on the cell lines. Biological results are here reported and discussed in terms of the structure-activity relationship.

Rational design of gold(III)-dithiocarbamato peptidomimetics for the targeted anticancer chemotherapy

As a further extension of our research work focusing on the development of gold(III)-dithiocarbamato dtc derivatives of oligopeptides as potential anticancer agents, complexes [AuIIIX2(dtc-Sar-l-Ser(t-Bu)- O(t-Bu))] (X = Br (1a)/Cl (

ENZYME INHIBITORS

Compounds of formula (I), inhibit HDAC activity: wherein A, B and D independently represent =CH- or =N-; W is-CH=CH- Or -CH2CH2-; R1 is a carboxylic acid group (-COOH), or an ester group which is hydrolysable by one or more intracellular carboxylesterase enzymes to a carboxylic acid group; R2 and R3 are selected from the side chains of a natural or non-natural alpha amino acid, provided that neither R2 nor R3 is hydrogen, or R2 and R3, taken together with the carbon to which they are attached, form a 3-6 membered saturated cycloalkyl or heterocyclyl ring; Y is a bond, -C(=O)-, -S(=O)2-, -C(=O)O-, -C(=O)NR'-, -C(=S)-NR', -C(=NH)NR' or -S(=O)2NR - wherein R' is hydrogen or optionally substituted C1-C6 alkyl; L1 is a divalent radical of formula -(Alk1)m(Q)n(Alk2)p- wherein m, n, p, Q, AIk1 and AIk2 are as defined in the claims; X1 represents a bond; -C(=O); or -S(=O)2-; -NR4C(=O)-, -C(=O)NR4-,- NR4C(=O)NR5-, -NR4S(=O)2-, or -S(=O)2NR4- wherein R4 and R5 are independently hydrogen or optionally substituted C1-C6 alkyl; and z is 0 or 1.

ENZYME AND RECEPTOR MODULATION

Covalent conjugates of an α,α-disubstituted glycine ester and a modulator of the activity of a target intracellular enzyme or receptor, wherein the ester group of the conjugate is hydrolysable by one or more intracellular carboxylesterase enzymes to the corresponding acid and the α,α-disubstituted glycine ester is conjugated to the modulator at a position remote from the binding interface between the inhibitor and the target enzyme or receptor pass into cells and the active acid hydrolysis product accumulates within the cells.

INHIBITORS OF P38 MAP KINASE

Compounds of formula (I) are p38 MAP kinase inhibitors useful for the treatment of autoimmune and inflammatory diseases: wherein: G is -N= or -CH=; D is an optionally substituted divalent mono- or bi-cyclic aryl or heteroaryl radical having 5 - 13 ring members; R6 is hydrogen or optionally substituted CrC3 alkyl; P represents hydrogen and U represents a radical of formula (IA); or U represents hydrogen and P represents a radical of formula (IA); wherein A represents an optionally substituted divalent mono- or bicyclic carbocyclic or heterocyclic radical having 5 - 13 ring members; z is O or 1; -X1-L1-Y- is a linker radical or bond; R1 is a carboxylic acid group (-COOH), or an ester group which is hydrolysable by one or more intracellular esterase enzymes to a carboxylic acid group; and R2 and R3 are as defined in the claims.

SUBSTITUTED THIOPHENECARBOXAMIDES AS IKK-BETA SERINE-, THREONINE-PROTEIN KINASE INHIBITORS

Compounds of formula (IA) or (IB) are IKK inhibitors useful in the treatment of autoimmune and inflammatory diseases: wherein R7 is hydrogen or optionally substituted (C1-C6)alkyl; A is an optionally substituted aryl or heteroaryl of 5-13 ring atoms; Z is a radical of formula R1C( R2)(R3)NH-Y-L1-X1-(CH2)z- wherein R1 is a carboxylic acid group (-COOH), or an ester group which is hydrolysable by one or more intracellular esterase enzymes to a carboxylic acid group; and R2 and R3 independently represent the side chain of a natural or non-natural alpha amino acid but neither of R2 and R3 is hydrogen, or R2 and R3 taken together with the carbon atom to which they are attached form a C3-C7 cycloalkyl ring, and z, Y, L1 and X1 are as defined in the claims.

Preferred conformations of peptides containing tert-leucine, a sterically demanding, lipophilic α-amino acid with a quaternary side-chain C β atom

Terminally protected homopeptides of tert-leucine, from the dimer to the bexamer, co-oligopeptides of tert-leucine in combination with α-aminoisobutyric acid or glycine residues up to the hexamer level, and simple dipeptides representing known scaffolds for catalysts in asymmetric organic reactions were prepared by solution methods and fully characterized. The results of conformation analysis, performed by use of FT-IR absorption, NMR, CD, and X-ray diffraction techniques, indicate that this Hydrophobic α-amino acid with tetrasubstitution at the Cβ atom is structurally versatile. We show that it prefers extended or semiextended conformations, but can also be accommodated in folded structures, pro vided that these are biased by the presence of helicogenic residues. The current large-scale production of Tle, combined with its conformational preferences unravelled in this work, should make this bulky, hydrophobic, C α-trisubstituted α-amino acid a regular building block of any strategy seeking to tailor peptides with improved catalytic and pharmacological properties.

An oxidative transformation of N′-phenylhydrazide to t-butyl ester using a copper(II) halide-lithium t-butoxide system

Reactions of hydrazides or N1-phenylhydrazides with a copper(II) reagent prepared from copper(II) bromide and lithium t-butoxide smoothly proceeded to give the corresponding t-butyl ester in high yield.

SYNTHESE VON 2-METHYLALANIN-PEPTIDEN, DIE pH-ABHAENGIGKEIT IHRER 13C-NMR-SPECTREN UND EINE NEUE METHODE ZUR AUSWERTUNG UEBER CS-DIAGRAMME

The uncommon amino-acid 2-methylalanine (α-aminoisobutiryc acid, Aib) was investigated by 13C-NMR.The chemical shifts of amino- or carboxy-protected derivates of Aib and of protected oligopeptides are discussed with respect to neighbouring groups and amino acids.The pH-dependence of the 13C-NMR spectra of Aib, Aib-Ala, Ala-Aib, Aib-Ala-Aib and Aib-Ala-Aib-Ala-Aib was studied.Using these examples, a new and advantageous method is demonstrated for the first time for the evaluation of NMR titration curves, which uses so-called chemical shift diagrams (CS diagrams).