163210-89-7

Usage

Uses

Used in Pharmaceutical Synthesis:
Tert-butyl (S)-2-[(tert-butoxycarbonyl)amino]-4-bromobutanoate is used as an intermediate in the synthesis of pharmaceuticals for its ability to facilitate the creation of complex organic molecules. Its presence in the synthesis process aids in the formation of desired compounds with specific biological activities.
Used in Organic Chemistry:
In the realm of organic chemistry, tert-butyl (S)-2-[(tert-butoxycarbonyl)amino]-4-bromobutanoate is used as a protecting group for amines. This application is crucial in multi-step synthesis processes where the amine group needs to be protected from unwanted reactions until the final steps of the synthesis.
Used in Research and Development:
tert-butyl (S)-2-[(tert-butoxycarbonyl)amino]-4-bromobutanoate is also utilized in research and development settings to explore new methods and pathways in organic synthesis, potentially leading to the discovery of novel pharmaceutical agents or improving existing synthesis techniques for enhanced efficiency and yield.
Used in Specialty Chemical Production:
Tert-butyl (S)-2-[(tert-butoxycarbonyl)amino]-4-bromobutanoate may be employed in the production of specialty chemicals that require its unique structural features for specific applications, such as in the development of new materials with tailored properties for various industries.

Upstream product

• 34582-32-6 N-tert-butoxycarbonyl aspartic acid tert-butyl ester 
• 41088-86-2 L-2-(tert-butyloxycarbonylamino)-4-hydroxybutyric acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 98946-18-0 tert-Butyl 2,2,2-trichloroacetimidate 
• 168264-01-5 tert-butyl (2S)-2-(tert-butoxycarbonylamino)-4-(methanesulfonyloxy)butanoate 
• 81323-58-2 N-(tert-butyloxycarbonyl)-(S)-homoserine tert-butyl ester 
• 34582-31-5 1-tert-butyl 4-methyl (S)-2-{[(tert-butoxy)carbonyl]amino}butanedioate 
• 59768-74-0 (S)-2-t-butoxycarbonylaminosuccinic acid 4-methyl ester 
• 24277-39-2 N-tert-butoxycarbonyl glutamic acid tert-butyl ester 

Downstream Products

• 1407507-06-5 di-tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-[4-(2-fluoroethoxy)benzyl]-hexanedioate 
• 1407507-31-6 di-tert-butyl (5S)-2-[4-(benzyloxy)benzyl]-2-(benzyloxycarbonyl)-5-[(tert-butoxy-carbonyl)amino]hexanedioate 
• 1408443-98-0 di-tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-(4-{[(4S,5S)-2,2-dimethyl-5-({[(4-methylphenyl)sulfonyl]oxy}methyl)-1,3-dioxolan-4-yl]methoxy}benzyl)hexanedioate 
• 1408443-93-5 di-tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-{4-[(tert-butoxycarbonyl)(2-((methylsulfonyl)oxy)ethyl)amino]benzyl}hexanedioate 
• 1408449-65-9 di-tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-{4-[(tert-butoxycarbonyl)(2-hydroxy-ethyl)amino]benzyl}hexanedioate 
• 1408449-63-7 di-tert-butyl (5S)-2-(4-{[2-(benzyloxy)ethyl](tert-butoxycarbonyl)amino}benzyl)-5-[(tert-butoxycarbonyl)amino]hexanedioate 
• 1408449-59-1 di-tert-butyl (5S)-2-(4-{[2-(benzyloxy)ethyl]amino}benzyl)-5-[(tert-butoxycarbonyl)-amino]hexanedioate 
• 1408447-46-0 di-tert-butyl (5S)-2-(4-aminobenzyl)-5-[(tert-butoxycarbonyl)amino]hexanedioate 
• 1408449-57-9 (5S)-2-(4-aminobenzyl)-6-tert-butoxy-2-(tert-butoxycarbonyl)-5-[(tert-butoxycarbonyl)-amino]-6-oxohexanoic acid 
• 1408447-80-2 (2S,5R)-2-tert.-butoxycarbonylamino-5-(4-hydroxy-benzyl)-hexanedioic acid di-tert.-butyl ester 
• 1408447-83-5 (2S,5S)-2-tert.-butoxycarbonylamino-5-(4-hydroxy-benzyl)-hexanedioic acid di-tert.-butyl ester 
• 1408447-04-0 (2S)-2-tert-butoxycarbonylamino-5-{2-[4-(2-fluoro-ethoxy)-phenyl]-ethyl}hexanedioic acid di-tert-butyl ester 
• 1408447-37-9 di-tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-[2-(4-hydroxyphenyl)ethyl]hexanedioate 
• 1408448-99-6 (5S)-6-tert-butoxy-2-(tert-butoxycarbonyl)-5-[(tert-butoxycarbonyl)amino]-2-[2-(4-hydroxyphenyl)ethyl]-6-oxohexanoic acid 

Relevant academic research and scientific papers

Efficient synthesis of hydrocarbon-bridged diaminodiacids through nickel-catalyzed reductive cross-coupling

Solid-phase incorporation of pre-prepared diaminodiacids has been established as an efficient strategy for the chemical synthesis of peptide disulfide bond mimics. Hydrocarbon-bridged diaminodiacids represent one important category of diaminodiacids but they remain difficult to synthesize. In the present work, we reported the use of newly-developed nickel catalyzed reductive cross-coupling reaction to efficiently synthesize diaminodiacids with hydrocarbon bridges. Through optimization of the reaction conditions, the yield of the hydrocarbon bridge formation reached about 50%, even when the reaction was scaled up to the gram level. Subsequently, using our recently developed Dmab/ivDde protecting group system, we obtained a new hydrocarbon-bridged diaminodiacid that are suitable for metal-free deprotection conditions. We demonstrated the utility of this Dmab/ivDde protected hydrocarbon-bridged diaminodiacid in the synthesis of a disulfide surrogate of oxytocin.

Trifluoroselenomethionine: A New Unnatural Amino Acid

Trifluoroselenomethionine (TFSeM), a new unnatural amino acid, was synthesized in seven steps from N-(tert-butoxycarbonyl)-l-aspartic acid tert-butyl ester. TFSeM shows enhanced methioninase-induced cytotoxicity, relative to selenomethionine (SeM), toward HCT-116 cells derived from human colon cancer. Mechanistic explanations for this enhanced activity are computationally and experimentally examined. Comparison of TFSeM and SeM by selenium EXAFS and DFT calculations showed them to be spectroscopically and structurally very similar. Nonetheless, when two different variants of the protein GB1 were expressed in an Escherichia coli methionine auxotroph cell line in the presence of TFSeM and methionine (Met) in a 9:1 molar ratio, it was found that, surprisingly, 85 % of the proteins contained SeM residues, even though no SeM had been added, thus implying loss of the trifluoromethyl group from TFSeM. The transformation of TFSeM into SeM is enzymatically catalyzed by E. coli extracts, but TFSeM is not a substrate of E. coli methionine adenosyltransferase.

Facile synthesis of Fmoc-protected phosphonate pSer mimetic and its application in assembling a substrate peptide of 14-3-3 ζ

Phosphatase-inert peptidomimetics containing phosphonate pSer analogue have been developed as valuable biological tools for probing and regulating pSer-dependent protein-protein interactions (PPIs) in cellular context. Herein, we report a facile and efficient synthesis route of Fmoc-protected phosphonate pSer mimetic and also present the application of this building block in the solid-phase synthesis of a phosphatase-resistant substrate peptide of 14-3-3 ζ, retaining 14-3-3 ζ binding efficacy similar to the parent pSer-containing peptide.

Chemical synthesis of disulfide surrogate peptides by using beta-carbon dimethyl modified diaminodiacids

The replacement of disulfide bridges with metabolically stable isosteres is a promising strategy to improve the stability of disulfide-rich polypeptides towards reducing agents and isomerases. A diaminodiacid-based strategy is one of the most effective methods to construct disulfide bond mimics, but modified diaminodiacids have not been developed till now. Inspired by the fact that alkylation of disulfide bonds can regulate the activity of polypeptides, herein, we report the first example of thioether bridged diaminodiacids incorporating Cys Cβdimethyl modification, obtained by penicillamine (Pen)-based thiol alkylation. The utility of these new diaminodiacids was demonstrated by the synthesis of disulfide surrogates of oxytocin containing a short-span disulfide bond and of KIIIA with large-span disulfide bonds. This new type of synthetic bridge further extends the diaminodiacid toolbox to facilitate the study of the structure-activity relationship of disulfide-rich peptides.

Diaminodiacid bridge improves enzymatic and in vivo inhibitory activity of peptide CPI-1 against botulinum toxin serotype A

The replacement of the disulfide bridge of CPI-1, a peptide inhibitor of light chain of Botulinum toxin serotype A, with the thioether-containing and biscarba-containing diaminodiacid bridge leads to a significant decrease in the degradation by trypsin and increase in the detoxification activity in vivo, the addition of hydrophobic or positive amino acid at C-terminus of modified peptides further improves the inhibitory activity.

Environmentally-friendly orthogonally protected diaminodiacid compound, and preparation method and application thereof

The invention discloses an environmentally-friendly orthogonally protected diaminodiacid compound, and a preparation method and an application thereof. The structural formula of the environmentally-friendly orthogonally protected diaminodiacid compound is

Preparing phosphorylated serine phosphonic acid mimetics of the method (by machine translation)

The invention relates to preparing phosphorylated serine phosphonic acid mimetics of the method, in particular, the method comprises: (1) the formula 1 as shown in the reduction reaction, in order to obtains the type 2 illustrated compound; (2) causes to state the type 2 as shown in performing the bromination reaction, in order to obtains the type 3 illustrated compound; (3) causes to state the type 3 a compound of the formula 4 compound shown in contact, in order to obtains the type 5 illustrated compound; (4) causes to state the type 5 as shown in the de-protecting group, in order to obtains the type (I) the compounds of formula, wherein R is hydrogen, benzyl, O-nitryl phenmethyl, coumarin or allyl, R1is benzyl, O-nitryl phenmethyl, coumarin or allyl. The method adopted by the raw materials are cheap, easy to obtain, the reaction route steps are less, the overall yield of the whole route in 20% or more, can be prepared to obtain high yield and high quality of the phosphorylated serine phosphonic acid mimetics. (by machine translation)

RADIOLABELED AMINO ACIDS FOR DIAGNOSTIC IMAGING

This invention relates to novel compounds suitable for labeling by 18F and to the corresponding 18F labeled compounds themselves, 19F-fluorinated analogues thereof and their use as reference standards, methods of preparing such compounds, compositions comprising such compounds, kits comprising such compounds or compositions and uses of such compounds, compositions or kits for diagnostic imaging by Positron Emission Tomography (PET).

Radiolabeled amino acids for diagnostic imaging

This invention relates to novel compounds suitable for labeling by 18F and to the corresponding 18F labeled compounds themselves, 19F-fluorinated analogues thereof and their use as reference standards, methods of preparing such compounds, compositions comprising such compounds, kits comprising such compounds or compositions and uses of such compounds, compositions or kits for diagnostic imaging by Positron Emission Tomography (PET).