20866-46-0

Basic information

• Product Name: N,N'-Di-tert-butoxycarbonyl-L-histidine
• Synonyms: BOC-HIS(BOC);BOC-HIS(BOC)-OH;BOC-HIS(BOC)-OH BENZENE;BOC-HISTIDINE(BOC)-OH BENZENE;BOC-L-HIS(BOC)-OH BENZENE;N-ALPHA-TERT-BUTYLOXYCARBONYL-N-IM-TERT-BUTYLOXYCARBONYL-L-HISTIDINE BENZENE;N ALPHA,N(IM)-DI-T-BUTOXYCARBONYL-L-HISTIDINE;NALPHA,N(IM)-DI-TERT-BUTOXYCARBONYL-L-HISTIDINE
• CAS NO: 20866-46-0
• Molecular Formula: C₁₆H₂₅N₃O₆
• Molecular Weight: 355.39
• Product Categories: Amino Acid Derivatives;Amino Acids;Histidine [His, H];Boc-Amino Acids and Derivative;Boc-Amino acid series;peptides
• Mol File: 20866-46-0.mol

Chemical Properties

• Appearance: /
• Density: 1.22 g/cm³
• Storage Temp.: -15°C
• PKA: 3.10±0.10(Predicted)
• CAS DataBase Reference: N,N'-Di-tert-butoxycarbonyl-L-histidine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-Di-tert-butoxycarbonyl-L-histidine(20866-46-0)
• EPA Substance Registry System: N,N'-Di-tert-butoxycarbonyl-L-histidine(20866-46-0)

Safety Data

• Hazardous Substances Data: 20866-46-0(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white crystalline powder

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 71-00-1 L-histidine 
• 17791-52-5 N-(tert-butoxycarbonyl)-L-histidine 
• 46924-53-2 1-tert-butoxycarbonyl-histidine 
• 71-00-1 L-histidine 
• 645-35-2 L-histidine monohydrochloride 

Downstream Products

• 142843-13-8 4-<2-<2-<<(2R,3S)-3-<α,N^im-bis(tert-butoxycarbonyl)-L-histidyl>amino>-4-cyclohexyl-2-hydroxy-1-butyl>sulfonyl>acetamido>ethyl>morpholine 
• 84043-93-6 di-tert-butoxycarbonylhistidine pentafluorophenylester 
• 85974-21-6 N,N^Im-di-t-butoxycarbonyl-L-histidyl-L-glutaminyl-β-benzyl-L-aspartyl-L-phenylalanine 4-picolyl ester 
• 85990-82-5 N,N^Im-di-t-butoxycarbonyl-L-histidyl-L-glutaminyl-β-benzyl-L-aspartyl-L-phenylalanyl-L-asparaginyl-O-benzyl-L-seryl-L-alanine 4-picolyl ester 
• 161451-67-8 4-{(S)-2-[3-(3-Benzyloxycarbonylamino-propylcarbamoyl)-propylcarbamoyl]-2-tert-butoxycarbonylamino-ethyl}-imidazole-1-carboxylic acid tert-butyl ester 
• 161451-68-9 4-[(S)-2-((S)-1-{[(2-Benzyloxycarbonylamino-ethylcarbamoyl)-methyl]-carbamoyl}-ethylcarbamoyl)-2-tert-butoxycarbonylamino-ethyl]-imidazole-1-carboxylic acid tert-butyl ester 
• 161451-69-0 4-[(S)-2-((R)-1-{[(2-Benzyloxycarbonylamino-ethylcarbamoyl)-methyl]-carbamoyl}-ethylcarbamoyl)-2-tert-butoxycarbonylamino-ethyl]-imidazole-1-carboxylic acid tert-butyl ester 
• 870-46-2 t-butoxycarbonylhydrazine 
• 17791-52-5 N-(tert-butoxycarbonyl)-L-histidine 
• 126301-48-2 Boc-His(Boc)-His-Glu(OBzl)-Ala-Opac 
• 126301-47-1 Boc-His(Boc)-Glu(OBzl)-Ala-OPac 
• 25616-02-8 Nα, Nim-di-Boc-L-histidine N-hydroxysuccinimide ester 
• 2387-23-7 1,3-Dicyclohexylurea 
• 205316-11-6 N,N'-bis[N^α,N^im-di(tert-butoxycarbonyl)-L-histidyl]ethane-1,2-diamine 

Relevant articles and documents

Synthesis method of N alpha-tert-butyloxycarbonyl-L-histidine

The invention relates to a synthesis method of N alpha-tert-butyloxycarbonyl-L-histidine, which comprises the following steps of: dissolving solid L-histidine in a sodium carbonate water solution, dropwisely adding liquid di-tert-butyl dicarbonate, reacting, filtering, and washing the filtrate with an organic solvent to remove unreacted di-tert-butyl dicarbonate; after the reaction solution is subjected to aqueous phase acidification, adding an extracting agent ethyl acetate for extraction, conducting standing and layering, and washing, drying and filtering an oil phase to obtain an ethyl acetate solution containing an intermediate N alpha-tert-butyloxycarbonyl-Nim-tert-butyloxycarbonyl-L-histidine; stirring the ethyl acetate solution containing the intermediate N alpha-tert-butyloxycarbonyl-Nim-tert-butyloxycarbonyl-L-histidine at 50-100 DEG C for reaction, and after the reaction is finished, carrying out after-treatment to obtain the product N alpha-tert-butyloxycarbonyl-L-histidine.The synthesis method of N alpha-tert-butyloxycarbonyl-L-histidine provided by the invention is simple in process and convenient to operate, the product purity and yield are higher than those in the prior art, the technical problem that purification and desalination are not thorough by using ion exchange resin is solved, and the synthesis method is suitable for industrial production.

MITOCHONDRIA-TARGETING PEPTIDES

Disclosed are non-natural peptides useful for the treatment and prevention of ischemia-reperfusion injury (e.g., cardiac ischemia-reperfusion injury) or myocardial infarction.

Rhamnolipid inspired lipopeptides effective in preventing adhesion and biofilm formation of Candida albicans

Rhamnolipids are biodegradable low toxic biosurfactants which exert antimicrobial and anti-biofilm properties. They have attracted much attention recently due to potential applications in areas of bioremediation, therapeutics, cosmetics and agriculture, however, the full potential of these versatile molecules is yet to be explored. Based on the facts that many naturally occurring lipopeptides are potent antimicrobials, our study aimed to explore the potential of replacing rhamnose in rhamnolipids with amino acids thus creating lipopeptides that would mimic or enhance properties of the parent molecule. This would allow not only for more economical and greener production but also, due to the availability of structurally different amino acids, facile manipulation of physico-chemical and biological properties. Our synthetic efforts produced a library of 43 lipopeptides revealing biologically more potent molecules. The structural changes significantly increased, in particular, anti-biofilm properties against Candida albicans, although surface activity of the parent molecule was almost completely abolished. Our findings show that the most active compounds are leucine derivatives of 3-hydroxy acids containing benzylic ester functionality. The SAR study demonstrated a further increase in activity with aliphatic chain elongation. The most promising lipopeptides 15, 23 and 36 at 12.5 μg/mL concentration allowed only 14.3%, 5.1% and 11.2% of biofilm formation, respectively after 24 h. These compounds inhibit biofilm formation by preventing adhesion of C. albicans to abiotic and biotic surfaces.

Tertiary-butoxycarbonyl (Boc) – A strategic group for N-protection/deprotection in the synthesis of various natural/unnatural N-unprotected aminoacid cyanomethyl esters

A number of cyanomethyl esters of natural/unnatural aminoacids with un-protected amino functionality were synthesized because of their synthetic and medicinal importance. Critical N-Boc deprotection methods in the presence of labile (hydrolytic sensitivity) cyanomethyl functionality were screened thoroughly and it was found that readily available 4M HCl in 1,4-dioxane solution (2–4 equiv); acetonitrile, 0 °C, 2–4 h was a suitable condition. This condition was generalized and successfully applied to a variety of alkyl, alkynyl, aryl, heteroaryl, benzyl, azido, spiro amino acid cyanomethylesters irrespective of the nature of the amine (primary or secondary) and the distance between the amine and ester group to achieve final deprotected amino esters with high yield, and purity compared to other commonly known N-protecting groups (Cbz, Fmoc, Ac, Bn, Bz etc.). It was also demonstrated that N-Boc protected aminoacid cyanomethylesters are stable enough to carry out further functionalization compared to N-unprotected counterparts.

Synthesis of Histidine-Containing Oligopeptides via Histidine-Promoted Peptide Ligation

Histidine-containing peptides are valuable therapeutic agents for a treatment of neurodegenerative diseases. However, the synthesis of histidine-containing peptides is not trivial due to the potential of imidazole sidechain of histidine to act as a nucleophile if unprotected. A peptide ligation method utilizing the imidazole sidechain of histidine has been developed. The key imidazolate intermediate that acts as an internal acyl transfer catalyst during ligation is generated by deprotonation. Transesterification with amino acids or peptides tethered with C-terminal thioester followed by N→N acyl shifts led to the final ligated products. A range of histidine-containing dipeptides could be synthesized in moderate to good yields via this method without protecting the imidazole sidechain. The protocol was further extended to tripeptide synthesis via a long-range N→N acyl transfer, and tetrapeptide synthesis.

A cyclic dipeptide production method

The invention relates to a production method for cyclic dipeptide, and belongs to a natural compound synthesis technology. Cyclic (histidine-proline) dipeptide is prepared by a cooling varying-temperature synthesis and high-pressure high-temperature water phase cyclizing technology. The production method comprises the following steps: taking hydrochloride of histidine proline dipeptide methyl ester as a raw material, and synthesizing high-quality and high-purity cyclic histidine-proline dipeptide by a high-pressure high-temperature assisted method in water containing strong basic and weak acidic salt. Compared with a conventional methanol reflux method, the production method is time-saving, efficient, high in product yield and free of racemization phenomenon.

BENZIMIDAZOLE DERIVATIVES AS BROMODOMAIN INHIBITORS

Compounds of formula (I) and salts thereof: wherein R1, R2, R3, R4 are defined herein. Compounds of formula (I) and salts thereof have been found to inhibit the binding of the BET family of bromodomain proteins to, for example, acetylated lysine residues and thus may have use in therapy, for example in the treatment of autoimmune and inflammatory diseases, such as rheumatoid arthritis; and cancers.

Synthesis, characterization and in vitro photodynamic antimicrobial activity of basic amino acid-porphyrin conjugates

Photodynamic antimicrobial chemotherapy (PACT), as a novel and effective modality for the treatment of infection with the advantage of circumventing multidrug resistance, receives great attention in recent years. The photosensitizer is the crucial element in PACT, and cationic porphyrins have been demonstrated to usually be more efficient than neutral and negatively charged analogues towards bacteria in PACT. In this work, three native basic amino acids, l-lysine, l-histidine and l-arginine, were conjugated with amino porphyrins as cationic auxiliary groups, and 13 target compounds were synthesized. This paper reports their syntheses, structural characterizations, oil-water partition coefficients, singlet oxygen generation yields, photo-stability, as well as their photo inactivation efficacies against methicillin-resistant Staphylococcus aureus (MRSA), Escherichia coli and Pseudomonas aeruginosa in vitro. The preliminary structure-activity relationship was discussed. Compound 4i, with porphyrin bearing four lysine moieties, displays the highest photo inactivation efficacy against the tested bacterial strains at 3.91 1/4M with a low light dose (6 J/cm2), and it is stable in serum and lower cytotoxicity to A929 cells. These basic amino acid-porphyrin conjugates are potential photosensitizers for PACT.

GLP-2 compounds, formulations, and uses thereof

The present invention relates to novel human glucagon-like peptide-2 (GLP-2) peptides and human glucagon-like peptide-2 derivatives which have a protracted profile of action as well as polynucleotide constructs encoding such peptides, vectors and host cells comprising and expressing the polynucleotide, pharmaceutical compositions, uses and methods of treatment.

Metal complexes of imidazole ligands containing histamine-like donor sets: equilibrium, solution structure and hydrolytic activity

The equilibrium and structural properties of copper(II) and zinc(II) complexes of N,N'-di-L-histidylethane-1,2-diamine (dhen) and those of the strongly related histamine have been characterized by pH-metric and spectroscopic (UV/VIS, CD, EPR and NMR) methods.In both dhen systems a dimeric M2L2 species is dominant near the physiological pH, having bis(histamine-like) 2Nim, 2NH2 co-ordination.The MLH-2 complex, also formed in both systems above pH 10, has different structures with the two metal ions.A hydroxo mixed-ligand complex is formed in the case of zinc(II), while the base-consuming processes are assigned to metal-promoted deprotonation of amide nitrogens in the copper(II) system.Between these two dominant species (pH 7-10) tetrameric complexes are formed in each case (as suggested by the CD, EPR and NMR results), with the participation of imidazole-N1 (pyrrolic) nitrogen in the co-ordination.The catalytic activity of the zinc(II)-containing systems towards the hydrolysis of uridine 2',3'-cyclic monophosphate as nuclease model has been examined.The zinc(II)-histamine complexes efficiently catalyse the hydrolysis.A kinetic study performed at different pH, concentrations and metal-to-ligand ratios, combined with the equilibrium data, revaeled three reaction pathways involving Zn(OH), ZnL and ZnL(OH) complexes as active species, in order of activity ZnLZn(OH)ZnL(OH).