3392-09-4

Basic information

• Product Name: BOC-LEU-OSU
• Synonyms: N-ALPHA-T-BOC-L-LEUCINE N-HYDROXYSUCCINIMIDE ESTER;N-TERT-BUTOXYCARBONYL-L-LEUCINE-N-HYDROXYSUCCINIMIDE ESTER;BOC-LEU-OSU;BOC-LEUCINE-OSU;BOC-L-LEUCINE N-HYDROXYSUCCINIMIDE ESTER;BOC-L-LEUCINE HYDROXYSUCCINIMIDE ESTER;BOC-L-Leucine Osu;N-(tert-butoxycarbonyl)-L-leucine N-hydroxysuccin
• CAS NO: 3392-09-4
• Molecular Formula: C₁₅H₂₄N₂O₆
• Molecular Weight: 328.36
• EINECS: 222-232-3
• Product Categories: AMINOACIDS DERIVATIVES;Amino Acid Derivatives
• Mol File: 3392-09-4.mol

Chemical Properties

• Melting Point: 110-113 °C(lit.)
• Appearance: /
• Density: 1.2 g/cm³
• Refractive Index: 1.504
• Storage Temp.: −20°C
• PKA: 10.81±0.46(Predicted)
• BRN: 4538026
• CAS DataBase Reference: BOC-LEU-OSU(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-LEU-OSU(3392-09-4)
• EPA Substance Registry System: BOC-LEU-OSU(3392-09-4)

Safety Data

• WGK Germany: 3
• F: 3-10-21
• Hazardous Substances Data: 3392-09-4(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

InChI:InChI=1/C15H24N2O6/c1-9(2)8-10(16-14(21)22-15(3,4)5)13(20)23-17-11(18)6-7-12(17)19/h9-10H,6-8H2,1-5H3,(H,16,21)

Upstream product

• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 13139-15-6 Boc-Leu-OH 
• 96935-01-2 Isopropenyl Succinimido Carbonate 
• 74124-79-1 di(succinimido) carbonate 
• 115654-40-5 (S)-(-)-1,1-dimethylethyl <1-(aminomethyl)-3-methylbutyl>carbamate 
• 109687-65-2 (S)-(-)-1,1-dimethylethyl <3-methyl-1-<<(methylsulfonyl)oxy>methyl>butyl>carbamate 
• 142554-61-8 (S)-(-)-1,1-dimethylethyl <1-(azidomethyl)-3-methylbutyl>carbamate 
• 82010-31-9 (S)-(1-hydroxymethyl-3-methylbutyl)carbamic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 61-90-5 L-leucine 
• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 

Downstream Products

• 37571-12-3 N-tert-butoxycarbonyl-L-leucyl-L-(N-ε-benzyloxycarbonyl)lysine methyl ester 
• 66415-01-8 N-((tert-butoxycarbonyl)-L-leucyl)-L-alanine benzyl ester 
• 406712-39-8 Boc-Leu-Val-Val-Tyr-Pro-Gln-Ot-Bu 
• 406712-36-5 (S)-2-({(S)-1-[(S)-2-{(S)-3-tert-Butoxy-2-[(S)-2-((S)-2-tert-butoxycarbonylamino-4-methyl-pentanoylamino)-3-methyl-butyrylamino]-propionylamino}-3-(4-hydroxy-phenyl)-propionyl]-pyrrolidine-2-carbonyl}-amino)-4-carbamoyl-butyric acid tert-butyl ester 
• 406712-32-1 (S)-2-({(S)-1-[(S)-2-{(R)-3-(Acetylamino-methylsulfanyl)-2-[(S)-2-((S)-2-tert-butoxycarbonylamino-4-methyl-pentanoylamino)-3-methyl-butyrylamino]-propionylamino}-3-(4-hydroxy-phenyl)-propionyl]-pyrrolidine-2-carbonyl}-amino)-4-carbamoyl-butyric acid 
• 73401-65-7 (S)-2-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-4-methyl-pentanoic acid 
• 84863-67-2 (S)-t-butyl 1-(isopentylamino)-4-methyl-1-oxopentan-2-ylcarbamate 
• 905975-52-2 ((S)-1-{(S)-1-Benzyl-2-[2-benzyl-1,1-dioxo-1λ⁶-isothiazolidin-(5Z)-ylidene]-ethylcarbamoyl}-3-methyl-butyl)-carbamic acid tert-butyl ester 
• 905975-51-1 ((S)-1-{(S)-1-Benzyl-2-[2-benzyl-1,1-dioxo-1λ⁶-isothiazolidin-(5E)-ylidene]-ethylcarbamoyl}-3-methyl-butyl)-carbamic acid tert-butyl ester 
• 905975-54-4 ((S)-1-{(S)-1-Benzyl-2-[1,1-dioxo-2-phenyl-1λ⁶-[1,2]thiazinan-(6Z)-ylidene]-ethylcarbamoyl}-3-methyl-butyl)-carbamic acid tert-butyl ester 
• 905975-53-3 ((S)-1-{(S)-1-Benzyl-2-[1,1-dioxo-2-phenyl-1λ⁶-[1,2]thiazinan-(6E)-ylidene]-ethylcarbamoyl}-3-methyl-butyl)-carbamic acid tert-butyl ester 
• 905975-56-6 ((S)-1-{(S)-1-Benzyl-2-[2-benzyl-1,1-dioxo-1λ⁶-[1,2]thiazinan-(6Z)-ylidene]-ethylcarbamoyl}-3-methyl-butyl)-carbamic acid tert-butyl ester 
• 905975-55-5 ((S)-1-{(S)-1-Benzyl-2-[2-benzyl-1,1-dioxo-1λ⁶-[1,2]thiazinan-(6E)-ylidene]-ethylcarbamoyl}-3-methyl-butyl)-carbamic acid tert-butyl ester 
• 285131-17-1 2-[2-(2-tert-butoxycarbonylamino-4-methylsulfanyl-butyrylamino)-4-methyl-pentanoylamino]-3-phenyl-propionic acid 2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-ylmethyl ester 

Relevant articles and documents

Asymmetric 1,4-Addition Reactions Catalyzed by N-Terminal Thiourea-Modified Helical l-Leu Peptide with Cyclic Amino Acids

N-terminal thiourea-modified l-Leu-based peptide {(3,5-diCF3Ph)NHC(=S)-(l-Leu-l-Leu-Ac5c)2-OMe} with five-membered ring α,α-disubstituted α-amino acids (Ac5c) catalyzed a highly enantioselective 1,4-addition reaction between β-nitrostyrene and dimethyl malonate. The enantioselective reaction required only 0.5 mol % chiral peptide-catalyst in the presence of iPr2EtN (2.5 equiv.), and gave a 1,4-adduct with 93 % ee of an 85 % yield. As Michael acceptors, various β-nitrostyrene derivatives such as methyl, p-fluoro, p-bromo, and p-methoxy substituents on the phenyl group, 2-furyl, 2-thiophenyl, and naphthyl β-nitroethylenes could be applied. Furthermore, various alkyl malonates and cyclic β-keto-esters could be used as Michael donors. It became clear that the length of the peptide chain, a right-handed helical structure, amide N?Hs, and the N-terminal thiourea moiety play crucial roles in asymmetric induction.

2-AMINO-N-(AMINO-OXO-ARYL-LAMBDA6-SULFANYLIDENE)ACETAMIDE COMPOUNDS AND THEIR THERAPEUTIC USE

The present invention pertains generally to the field of therapeutic compounds. More specifically the present invention pertains to certain 2-amino-N-(amino-oxo-aryl-λ6- sulfanylidene)acetamide compounds (referred to herein as ANASIA compounds) that, inter alia, inhibit (e.g., selectively inhibit) bacterial aminoacyl-tRNA synthetase (aaRS) (e.g., bacterial leucyl-tRNA synthetase, LeuRS). The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit (e.g., selectively inhibit) bacterial aminoacyl-tRNA synthetase; to treat disorders that are ameliorated by the inhibition (e.g., selective inhibition) of bacterial aminoacyl-tRNA synthetase; to treat bacterial infections; etc.

Synthesis of pyrimidine nucleoside and amino acid conjugates

The synthesis of novel pyrimidine nucleoside bioconjugates with amino acids is presented. The N4-amino acid-acylated 2′-deoxycytidine analogues, modified with various amino acids, were synthesized using a three-step synthesis and obtained in moderate overall yields. Novel amino acid-alkylated 2′-deoxycytidine derivatives were obtained during the rearrangement of amino acid-acylated derivatives that occurred during Boc deprotection.

Binding and Action of Amino Acid Analogs of Chloramphenicol upon the Bacterial Ribosome

Antibiotic chloramphenicol (CHL) binds with a moderate affinity at the peptidyl transferase center of the bacterial ribosome and inhibits peptide bond formation. As an approach for modifying and potentially improving properties of this inhibitor, we explored ribosome binding and inhibitory activity of a number of amino acid analogs of CHL. The L-histidyl analog binds to the ribosome with the affinity exceeding that of CHL by 10 fold. Several of the newly synthesized analogs were able to inhibit protein synthesis and exhibited the mode of action that was distinct from the action of CHL. However, the inhibitory properties of the semi-synthetic CHL analogs did not correlate with their affinity and in general, the amino acid analogs of CHL were less active inhibitors of translation in comparison with the original antibiotic. The X-ray crystal structures of the Thermus thermophilus 70S ribosome in complex with three semi-synthetic analogs showed that CHL derivatives bind at the peptidyl transferase center, where the aminoacyl moiety of the tested compounds established idiosyncratic interactions with rRNA. Although still fairly inefficient inhibitors of translation, the synthesized compounds represent promising chemical scaffolds that target the peptidyl transferase center of the ribosome and potentially are suitable for further exploration.

New Class of Selective Estrogen Receptor Degraders (SERDs): Expanding the Toolbox of PROTAC Degrons

An effective endocrine therapy for breast cancer is to selectively and effectively degrade the estrogen receptor (ER). Up until now, there have been largely only two molecular scaffolds capable of doing this. In this study, we have developed new classes of scaffolds that possess selective estrogen receptor degrader (SERD) and ER antagonistic properties. These novel SERDs potently inhibit MCF-7 breast cancer cell proliferation and the expression of ER target genes, and their efficacy is comparable to Fulvestrant. Unlike Fulvestrant, the modular protein-targeted chimera (PROTAC)-type design of these novel SERDs should allow easy diversification into a library of analogs to further fine-tune their pharmacokinetic properties including oral availability. This work also expands the pool of currently available PROTAC-type scaffolds that could be beneficial for targeted degradation of various other therapeutically important proteins.

N,O-Bis(trimethylsilyl)acetamide/N-hydroxysuccinimide ester (BSA/NHS) as coupling agents for dipeptide synthesis

A method using N,O-bis(trimethylsilyl)acetamide/N-hydroxysuccinimide ester (BSA/NHS) as coupling agents for dipeptide synthesis is descried. The coupling reaction between N-hydroxysuccinimide (NHS) esters and amines could be performed under mild conditions with N,O-bis(trimethylsilyl)acetamide (BSA) as coupling reagent and no additional acid/base is required. All byproducts and excessive reactants are water soluble or hydrolysable and easy to eliminate through water-washing at the purification stage. Moreover, all the reactants are inexpensive and widely used in conventional drug production.

Bispidine as a secondary structure nucleator in peptides

Here we describe bispidine as a scaffold for inducing open turn-like and beta sheet conformations on the attached peptides depending on the mode of attachment of peptides to the scaffold. Various bispidine-peptide conjugates were designed and synthesized to demonstrate the versatility of the scaffold.

A facile synthesis and crystallographic analysis of N-protected β-amino alcohols and short peptaibols

A facile, efficient and racemization-free method for the synthesis of N-protected β-amino alcohols and peptaibols using N-hydroxysuccinimide active esters is described. Using this method, dipeptide, tripeptide and pentapeptide alcohols were isolated in high yields. The conformations in crystals of β-amino alcohol, dipeptide and tripeptide alcohols were analysed, with a well-defined type III β-turn being observed in the tripeptide alcohol crystals. This method is found to be compatible with Fmoc-, Boc- and other side-chain protecting groups.

Synthesis and biological evaluation of boron peptide analogues of Belactosin C as proteasome inhibitors

A series of boron peptides 11, 13, 15 and 17 were designed and synthesized as proteasome inhibitors based on the structure of Belactosin C. Matteson homologation was a key step in the synthesis of the boron peptides. Compounds 11a and 13 showed significant inhibition of 20S proteasome chymotrypsin-like (β5) activity (IC50 = 0.28 and 0.51 μM, respectively). Furthermore, like PS-341, compound 11a increased the G2/M cell distribution. A biparametric cytofluorimetric analysis with FITC-labeled annexin V and propidium iodide showed induction of apoptosis by compound 11a at >1 μM concentrations of compound.

Procedure for the oxidation of β-amino alcohols to α-amino aldehydes

A novel procedure for the mild oxidation of β-amino alcohols to α-amino aldehydes using commercially available manganese(IV) oxide is reported. There are several important advantages of the new method, such as high enantiopurity of the reaction and the absence of either over-oxidation or any reaction by-products during the process. A number of N-protected L-α-amino aldehydes was obtained. All new compounds were characterized by their NMR spectra and optical rotation data. Georg Thieme Verlag Stuttgart.