70717-76-9

Usage

Uses

Used in Pharmaceutical Development:
BOC-D-VAL-NH2 is used as a building block in the synthesis of peptides and proteins for pharmaceutical applications. The BOC protecting group allows for the controlled formation of peptide bonds, ensuring the correct sequence and structure of the final peptide product.
Used in Biochemical Research:
In biochemical research, BOC-D-VAL-NH2 is utilized as a component in the study of peptide and protein interactions, as well as in the development of new methods for peptide synthesis. The BOC group provides a means to control the reactivity of the amino group, facilitating the investigation of specific biochemical processes.
Used in Custom Peptide Production:
BOC-D-VAL-NH2 is used as a key ingredient in the production of custom peptides, which are tailored for specific applications in research, diagnostics, or therapeutics. The presence of the BOC group ensures that the amino group remains protected during the synthesis process, allowing for the precise assembly of the desired peptide sequence.

InChI:InChI=1/C10H20N2O3/c1-6(2)7(8(11)13)12-9(14)15-10(3,4)5/h6-7H,1-5H3,(H2,11,13)(H,12,14)/t7-/m1/s1

Upstream product

• 128211-52-9 (3S)-3-N-(tert-butyloxycarbonyl)amino-4-methylpentan-2-one 
• 22838-58-0 Boc-D-Val-OH 

Downstream Products

• 142055-86-5 (R)-(1-cyano-2-methyl-propyl)-carbamic acid tert-butyl ester 
• 1044661-22-4 1,1-dimethylethyl [2-(acryloyl{1-[4-cyano-5-methyl-6-oxo-1-(phenylmethyl)-1,6-dihydro-2-pyrimidinyl]-2-methylpropyl}amino)ethyl]carbamate 
• 851635-10-4 1,1-dimethylethyl [2-({1-[4-cyano-5-methyl-6-oxo-1-(phenylmethyl)-1,6-dihydro-2-pyrimidinyl]-2-methylpropyl}amino)ethyl]carbamate 
• 851635-07-9 5-methyl-2-[2-methyl-1-(7-oxohexahydro-1H-1,4-diazepin-1-yl)propyl]-6-oxo-1-(phenylmethyl)-1,6-dihydro-4-pyrimidinecarbonitrile 
• 1044661-23-5 N-(2-aminoethyl)-N-{1-[4-cyano-5-methyl-6-oxo-1-(phenylmethyl)-1,6-dihydro-2-pyrimidinyl]-2-methylpropyl}-2-propenamide 
• 625840-39-3 [1-(3-benzyl-5-methyl-6-cyano-4-oxo-3,4-dihydro-pyrimidin-2-yl)-2-methyl-propyl]-carbamic acid-t-butyl ester 
• 851635-09-1 2-(1-amino-2-methylpropyl)-5-methyl-6-oxo-1-(phenylmethyl)-1,6-dihydro-4-pyrimidinecarbonitrile 
• 32526-16-2 D-valine amide 
• 625840-35-9 [(R)-1-(N-benzyl-carbamimidoyl)-2-methyl-propyl]-carbamic acid t-butyl ester 
• 186453-48-5 2-((S)-1-{[2-((R)-1-{[2-(tert-Butoxycarbonylamino-methyl)-thiazole-4-carbonyl]-amino}-2-methyl-propyl)-thiazole-4-carbonyl]-amino}-ethyl)-5-methyl-oxazole-4-carboxylic acid pentafluorophenyl ester 

Relevant academic research and scientific papers

Synthesis of the Bycroft-Gowland structure of micrococcin P1

(formula presented) We describe the chemical synthesis of the accepted structure of micrococcin P1, a member of the thiostrepton group of antibiotics, and we show that this architecture does not correspond to that of the natural product. Methods developed during the present study should greatly facilitate ongoing efforts centering on the determination of the actual structure of microccin P1, in addition to being applicable to the synthesis of more complex thiostrepton congeners.

Amidation of carboxylic acids via the mixed carbonic carboxylic anhydrides and its application to synthesis of antidepressant (1S,2R)-tranylcypromine

Primary amidations of carboxylic acids 1 or 3 with NH4Cl in the presence of ClCO2Et and Et3N were developed to afford the corresponding primary amides in 22% to quantitative yields. Additionally, we have applied the amidation to the preparation of various amides containing hydroxamic acids and achieved the synthesis of (1S,2R)-tranylcypromine as an antidepressant medicine via Lossen rearrangement.

RITA Mimics: Synthesis and Mechanistic Evaluation of Asymmetric Linked Trithiazoles

The established cytotoxic agent RITA contains a thiophene-furan-thiophene backbone and two terminal alcohol groups. Herein we investigate the effect of using thiazoles as the backbone in RITA-like molecules and modifying the terminal groups of these trithiazoles, thereby generating 41 unique structures. Incorporating side chains with varied steric bulk allowed us to investigate how size and a stereocenter impacted biological activity. Subjecting compounds to growth inhibition assays on HCT-116 cells showed that the most potent compounds 7d, 7e, and 7h had GI50 values of 4.4, 4.4, and 3.4 μM, respectively, versus RITA (GI50 of 800 nM). Analysis of these compounds in apoptosis assays proved that 7d, 7e, and 7h were as effective as RITA at inducing apoptosis. Evaluating the impact of 7h on proteins targeted by RITA (p53, c-Myc, and Mcl-1) indicated that it acts via a different mechanism of action to that of RITA. RITA suppressed Mcl-1 protein via p53, whereas compound 7h suppressed Mcl-1 expression via an alternative mechanism independent of p53.

Studies on the synthesis of peptides containing dehydrovaline and dehydroisoleucine based on copper-mediated enamide formation

The preparation of peptide fragments containing dehydrovaline and dehydroisoleucine moieties present in the antibiotic myxovalargin is reported. Peptide formation is based on a copper-mediated C-N cross-coupling protocol between an acyl amide and a peptidic vinyl iodide. The presence of a neighboring arginine in the vinyl iodide posed a challenge with respect to the choice of the protecting group and the reaction conditions. It was found that ornithine - a suitable precursor - is better suited than arginine for achieving good yields for the C-N cross-coupling reaction. The optimized conditions were utilized for the synthesis of peptides 32, 33, 39 and 40 containing a neighboring ornithine as well as for the tripeptide 44 containing dehydroisoleucine with the correct stereochemistry.

Total synthesis and complete structural assignment of Yaku'amide A

Here we report the first total synthesis and the complete stereochemical assignment of yaku'amide A. Yaku'amide A (1) was isolated from a sponge Ceratopsion sp. as an extremely potent cytotoxin. Its structure was determined except for the C4-stereochemist

2-(N-Benzyl-N-phenylsulfonamido)alkyl amide derivatives as γ-secretase inhibitors

A series of (N-benzyl-N-phenylsulfonamido)alkyl amides were developed from classic and parallel synthesis strategies. Compounds with good in vitro and in vivo γ-secretase activity were identified and described.

Synthesis of the thiazole-thiazoline fragment of largazole analogues

The thiazole - thiazoline fragment of the marine natural product largazole, a potent histone deacetylase 1 inhibitor, has been synthesized in five steps. The methodology provides rapid access to thiazole-4-carbonitrile, thiazole-4-carbimidate, thiazole -

The preparation of optically active α-amino 4H-[1,2,4]oxadiazol-5-ones from optically active α-amino acids

Optically active α-amino 4H-[1,2,4]oxadiazol-5-ones (oxadiazolones) were prepared from optically active α-amino acids in five synthetic steps. The oxadiazolone moiety serves as a bioisosteric replacement for the carboxylic acid. Incorporation of an α-amino oxadiazolone into a representative dipeptide mimic is described.

Substituted benzofused heterocycles

The present invention relates to the compounds of Formula I, their preparation and pharmaceutical compositions comprising them. The compounds and pharmaceutical compositions are useful, for example, for the treatment and prevention of obesity, obesity-related disorders and eating disorders.

COMPOUNDS, COMPOSITIONS, AND METHODS

Compounds useful for treating cellular proliferative diseases and disorders by modulating the activity of KSP are disclosed.