45159-34-0

Usage

Chemical Properties

White powder

Uses

Boc-beta-cyano-l-alanine

InChI:InChI=1/C9H14N2O4/c1-9(2,3)15-8(14)11-6(4-5-10)7(12)13/h6H,4H2,1-3H3,(H,11,14)(H,12,13)/t6-/m0/s1

Upstream product

• 7536-55-2 N-tert-butyloxycarbonylasparagine 

Downstream Products

• 190447-69-9 Nα-Boc-L-2,4-diaminobutyric acid tert-butyl ester hydrochloride 
• 1425426-75-0 C₁₇H₂₁N₃O₅ 
• 335280-58-5 tert-butyl [(2S)-1-cyano-3-hydroxypropan-2-yl]carbamate 
• 1269406-91-8 1,1-dimethylethyl ((1S)-1-(cyanomethyl)-2-{[(3S)-1-(2-cyano-4-nitrophenyl)-3-pyrrolidinyl]amino}-2-oxoethyl)carbamate 
• 147091-70-1 methyl (S)-2-((t-butoxycarbonyl)amino)-3-cyanopropanoate 
• 126898-53-1 (S)-N-(tert-butoxycarbonyl)-N'-carbobenzoxy-3,3-diaminopropionamide 
• 126898-52-0 (S)-N-(tert-butoxycarbonyl)-N'-carbethoxy-3,3-diaminopropionitrile 
• 603137-45-7 C₂₈H₄₁N₇O₇S₂ 
• 174146-52-2 (R)-((S)-2-tert-Butoxycarbonylamino-3-cyano-propionylamino)-(3,5-dihydroxy-4-methoxy-phenyl)-acetic acid tert-butyl ester 
• 82215-22-3 Boc-L-β-cyanoalanine-3,4,5-trichlorophenyl ester 

Relevant academic research and scientific papers

IMIDAZOPYRIDINE DERIVATIVES AS PI3K INHIBITORS

New imidazopyridine derivatives having the chemical structure of formula (I) are disclosed; as well as process for their preparation, pharmaceutical compositions comprising them and their use in therapy as inhibitors of Phosphoinositide 3-Kinases (PI3Ks).

Design of potent inhibitors for Schistosoma japonica glutathione S-transferase

We implemented both structure-based drug design and the concept of polyvalency to discover a series of potent and unsymmetrical Schistosoma japonicum glutathione S-transferase (SjGST) inhibitors 10-12. This strategy achieved not only an excellent enhancement (10- to 490-fold) in the inhibitory potency, compared to the monofunctional analogues 1-5, but was also an effective modification by selecting a hydrophobic moiety with a flexible linker. The designed compounds with a low micromolar hit demonstrate special values in refining the new generation of SjGST inhibitors. The stoichiometry of the binding is one inhibitor molecule per SjGST monomer via isothermal titration calorimetric measurement.

Synthesis of the vancomycin CD and DE ring systems

Full details of the synthesis of the fully substituted vancomycin CD and DE ring systems are described and a potential solution to the control of the atropisomer stereochemistry is defined.

Discovery of an orally active series of isoxazoline glycoprotein IIb/IIIa antagonists

Using isoxazoline XR299 (la) as a starting point for the design of highly potent, long-duration GPIIb/IIIa antagonists, the effect of placing lipophilic substituents at positions α and β to the carboxylate moiety was evaluated. Of the compounds studied, it was found that the n-butyl carbamate 24u1,2 exhibited superior potency and duration of ex vivo antiplatelet effects in dogs. Replacement of the benzamidin-4-yl moiety with alternative basic groups, elimination of the isoxazoline stereocenter, and reversal of the orientation of the isoxazoline ring resulted in lowered potency and/or duration of action.

Synthesis, Biological Testing, and Stereochemical Assignment of an End Group Modified Retro-Inverso Bombesin C-Terminal Nonapeptide

The end group modified retro-inverso bombesin C-terminal nonapeptide 3 and its diastereomer 4 have been synthesized.The absolute configurations at the substituted malonamic acid residues in 3 and 4 were determined by chemical correlations with D- and L-2-aminobutyric acids of known absolute configuration.Thus, the absolute configuration at the substituted malonic acid residues in each diastereomer of 25a were determined by Raney nickel desulfurization followed by Hofmann degradation to give the dipeptide derivatives 30 and 31 having established absolute configurations.Hydrolysis of 25a then gave the diastereomeric acids 25b having defined stereochemistries.Coupling of the diastereomer of 25b having the R configuration at the substituted malonamic acid residue to the hexapeptide 27 then gave a stereochemically defined diastereomer of 19, which was converted to 20b.Deprotection of 20a and 20b gave 3 and 4, respectively.As shown by an assay that measures the increase in inositol phosphates in GH3 rat pituitary cells stimulated by bombesin-like peptides, the retro-inverso peptide 3, having an absolute configuration at the substituted malonic acid residue corresponding to that of the methionine residue in bombesin, was essentially inactive as an agonist, whereas peptide 4, having the opposite configuration at the substituted malonamic acid residue, had weak agonist activity when compared to that of bombesin.Neither 3 nor 4 had any bombesin antagonist activity.

AMINO ACID SURROGATES : AN INDIRECT METHOD FOR THE SYNTHESIS OF PEPTIDES CONTAINING THE THIOASPARAGINYL RESIDUE

The protected pentapeptide, Boc-Tan-Cys(PMB)-Pro-Leu-GlyNH2 and related thioasparaginyl compounds were prepared by an indirect method from their corresponding β-cyanoalanyl precursors by treatment with H2S/NH3.The optical purities of thioasparagine (Tan)

A Quantitative Evaluation of Methods for Coupling Asparagine

A quantitative procedure was developed to evaluate methods for coupling asparagine.Boc-asparagine was coupled to glycyloxymethylphenoxymethyl-copoly(styrene-divinylbenzene) resin under a variety of conditions, and the product, Asn-Gly, and any byproducts were cleaved from the resin with 50percent trifluoroacetic acid in methylene chloride.The mixture was then separated on a sulfonated ion exchange column and quantitated by the ninhydrin reaction.Coupling by the dicyclohexylcarbodiimide (DCC) or symmetrical anhydride methods gave large amounts of the dehydration product, β-cyanoalanylglycine, and smaller amounts of β-aspartamidinoacetic acid, α-aspartylglycine, and β-aspartylglycine in addition to the desired asparaginylglycine.Activation of Boc-Asn by DCC plus hydroxybenzotriazole or by the nitrophenyl ester gave 98 to 99percent of Asn-Gly, but very low levels of the byproducts were detectable with the sensitive chromatographic method.Protection of the amide function of Boc-Asn with the 4,4'-dimethoxybenzhydryl group avoided completely the formation of the nitrile during DCC coupling.Pure Ala(CN)-Gly was quantitatively reconverted to Asn-Gly by HF.The rehydration of nitrile also occurred in 50percent trifluoroacetic acid in dichloromethane, but much more slowly.