53308-95-5

Usage

Uses

Used in Pharmaceutical Industry:
BOC-NVA-OH is used as a key component in the synthesis of α-amino acid ester prodrugs for their cytotoxic effects against human lung cancer. Its chemical properties make it a valuable asset in the development of targeted therapies for cancer treatment, potentially improving patient outcomes and survival rates.

InChI:InChI=1/C10H19NO4/c1-5-6-7(8(12)13)11-9(14)15-10(2,3)4/h7H,5-6H2,1-4H3,(H,11,14)(H,12,13)/p-1/t7-/m0/s1

Upstream product

• 142729-70-2 D,L-N-Boc-nor-valine methyl ester 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 56926-94-4 methyl (2S)-2-[N-(t-butoxycarbonyl)amino]-3-(4-methylbenzenesulfonyl)-oxypropionate 
• 116611-52-0 [(R)-2-Benzenesulfonyl-1-(tetrahydro-pyran-2-yloxymethyl)-butyl]-carbamic acid tert-butyl ester 
• 116611-61-1 ((R)-2-Benzenesulfonyl-1-hydroxymethyl-butyl)-carbamic acid tert-butyl ester 
• 116611-44-0 ((R)-2-benzenesulfonyl-1-hydroxymethyl-ethyl)carbamic acid tert-butyl ester 
• 116611-43-9 (R)-2-tert-butyl carbamoyl-1-hydroxy-3-(phenylthio)propane 
• 116611-42-8 (R)-2-tert-butoxycarbonylamino-3-phenylsulfanylpropionic acid methyl ester 
• 116611-45-1 (2R)-2-t-butoxycarbonylamino-3-phenylsulfonyl-1-(2-tetrahydropyranyloxy)propane 
• 6600-40-4 L-Norvaline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 116611-57-5 tert-butyl [(1S)-1-(hydroxymethyl)butyl]carbamate 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 

Downstream Products

• 177659-58-4 (S)-1-((S)-2-tert-Butoxycarbonylamino-pentanoyl)-pyrrolidine-2-carboxylic acid benzyl ester 
• 108233-37-0 N-t-BOC-L-Nor-N-hydroxysuccinimide 
• 566939-07-9 (S)-2-tert-Butoxycarbonylamino-pentanoic acid (1S,2S)-2-benzyloxycarbonylamino-1-((R)-4-tert-butylcarbamoyl-thiazolidine-3-carbonyl)-3-phenyl-propyl ester 
• 625122-55-6 tert-butyl (1S)-(1-{[(benzenesulfonyl)amino]carbonyl}butyl)carbamate 
• 64896-37-3 methyl N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-norvalinate 
• 116611-57-5 tert-butyl [(1S)-1-(hydroxymethyl)butyl]carbamate 

Relevant academic research and scientific papers

Microporous Molecular Materials from Dipeptides Containing Non-proteinogenic Residues

Dipeptides with two hydrophobic side chains have proved to be an exceptional source of microporous organic materials, but since previous structures were limited to the incorporation of only proteinogenic residues, their full potential as adsorbents has remained unexplored. Single-crystal XRD data for ten new compounds with non-proteinogenic L-2-aminobutanoic acid and/or L-2-amino-pentanoic acid are presented. The gas-phase accessibility of their crystal pores, with cross-sections of 2.3 to 5.1?, was monitored by CO2 and CH4 adsorption isotherms. Included CO2 was also detected spectroscopically by 2D MAS NMR. An extensive conformational analysis reveals that the use of linear rather than branched side chains (such as L-valine and L-isoleucine) affords peptides with a greater degree of conformational freedom and yields more-flexible channel surfaces that may easily adapt to a series of potential guest molecules.

Self-assembling dipeptide-based nontoxic vesicles as carriers for drugs and other biologically important molecules

Self-assembling short peptides can offer an opportunity to make useful nano-/microstructures that find potential application in drug delivery. We report here the formation of multivesicular structures from self-assembling water-soluble synthetic amphiphilic dipeptides containing a glutamic acid residue at the C-terminus. These vesicular structures are stable over a wide range of pH (pH 2-12). However, they are sensitive towards calcium ions. This causes the rupturing of these vesicles. Interestingly, these vesicles can not only encapsulate an anticancer drug and a fluorescent dye, but also can release them in the presence of calcium ions. Moreover, these multivesicular structures have the potential to carry biologically important molecules like cyclic adenosine monophosphate (cAMP) within the cells keeping their biological functions intact. A MTT cell-survival assay suggests the almost nontoxic nature of these vesicles. Thus, these peptide vesicles can be used as biocompatible delivery vehicles for carrying drugs and other bioactive molecules.

Enzymatic approach to both enantiomers of N-Boc hydrophobic amino acids

Protease catalysed hydrolysis of N-Boc-amino acid esters allows us to obtain N-Boc l-acids and d-esters of amino butanoic acid, nor-leucine, nor-valine, leucine and t-leucine in excellent ee. The reaction occurs in short reaction times and high concentrations. When a biphasic system (buffer-MTBE) is employed, a strong solvent effect is observed. This method could be of significance for the preparation of d-t-leucine, for which a practical method is currently unavailable.

Exploration of the P1 SAR of aldehyde cathepsin K inhibitors.

The synthesis and biological activity of a series of aldehyde inhibitors of cathepsin K are reported. Exploration of the properties of the S(1) subsite with a series of alpha-amino aldehyde derivatives substituted at the P(1) position afforded compounds with cathepsin K IC(50)s between 52 microM and 15 nM.

Synthesis of new indolactam analogues by microbial conversion

Ten indolactam congeners with L-Ala, Abu, γ,δ-Δ-Nva, Nva, Nle, tert-Leu, Leu, Ile, allo-Ile. Phg instead ofL-Val in (-)-indolactam-Val, were synthesized from their seco-compounds (N-methyl-L-amino acidyl-L-tryptophonol) by microbial conversion.

A NOVEL APPROACH TO THE SYNTHESIS OF OPTICALLY PURE NON PROTEIN α-AMINO ACIDS IN BOTH L AND D CONFIGURATIONS FROM L-SERINE

Efficient syntheses of (2R)-2-Boc-amino-3-phenylsulfonyl-1-propanol 3 and its enantiomer 9 from L-serine are described.The potential of these compounds in a novel general method for the synthesis of optically pure non protein α-amino acids in both the L and D configurations is exemplified by the preparation of N-Boc-L-and D-homophenylalanine,-norvaline and -norleucine.