57133-29-6

Basic information

• Product Name: BOC-ORN(BOC)-OH
• Synonyms: N,N'-DI-(TERT-BUTYLOXYCARBONYL)-L-ORNITHINE;N,N'-DI-(T-BUTYLOXYCARBONYL)-L-ORNITHINE;N-ALPHA,N-DELTA-DI-T-BUTOXYCARBONYL-L-ORNITHINE;N-ALPHA,DELTA-BIS-BOC-L-ORNITHINE;BOC-L-ORN(BOC);BOC-L-ORN(BOC)-OH;BOC-ORN(BOC)-OH;BOC-ORNITHINE(BOC)-OH
• CAS NO: 57133-29-6
• Molecular Formula: C₁₅H₂₈N₂O₆
• Molecular Weight: 332.39
• Mol File: 57133-29-6.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 504.1 °C at 760 mmHg
• Flash Point: 258.7 °C
• Appearance: /
• Density: 1.123 g/cm³
• Vapor Pressure: 1.58E-11mmHg at 25°C
• Storage Temp.: 2-8°C
• PKA: 3.96±0.21(Predicted)
• CAS DataBase Reference: BOC-ORN(BOC)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-ORN(BOC)-OH(57133-29-6)
• EPA Substance Registry System: BOC-ORN(BOC)-OH(57133-29-6)

Safety Data

• Hazardous Substances Data: 57133-29-6(Hazardous Substances Data)

Usage

Uses

Boc-Orn(Boc)-OH, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

InChI:InChI=1/C15H28N2O6/c1-14(2,3)22-12(20)16-9-7-8-10(11(18)19)17-13(21)23-15(4,5)6/h10H,7-9H2,1-6H3,(H,16,20)(H,17,21)(H,18,19)/p-1/t10-/m0/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 36630-89-4 (S)-α-ornithine hydrochloride 
• 3184-13-2 L-ornithine hydrochloride 
• 70-26-8 L-ornithine 

Downstream Products

• 160693-31-2 Boc-Orn(Boc)-Phe-OBzl 
• 160693-42-5 Boc-Orn(Boc)-Glu(OMe)-Phe-Gly-Leu-Met-NH₂ 
• 160693-40-3 Boc-Orn(Boc)-Asp(OBzl)-Phe-Gly-Leu-Met-NH₂ 
• 160693-41-4 Boc-Orn(Boc)-Glu(OBzl)-Phe-Gly-Leu-Met-NH₂ 
• 858368-18-0 [4-tert-butoxycarbonylamino-4-(4-sulfamoyl-benzylcarbamoyl)-butyl]-carbamic acid tert-butyl ester 
• 1254581-04-8 16-[4-(2,5-bis-[(tert-butoxycaronyl)amino]pentanoylamino)phenoxy]hexadecanoic acid methyl ester 
• 1254581-05-9 (1-{4-[15-(2-aminoethylcarbamoyl)pentadecyloxy]phenylcarbamoyl}-4-tert-butoxycabonylaminobutyl)carbamic acid tert-butyl ester 
• 1254581-06-0 [4-tert-butoxylamino-4-(4-{15-[2-(2,3,4,5,6-pentahydroxyhexanoylamino)ethylcabamoyl]pentadecyloxy}phenylcarbamoyl)butyl]carbamic acid tert-butyl ester 
• 1254581-07-1 16-[4-(2,5-diaminopentanoylamino)phenoxy]hexadecanoicacid[2-(2,3,4,5,6-pentahydroxyhexanoylamino)ethyl]amide 

Relevant articles and documents

Ornithine-derived oligomers and dendrimers forin vitrodelivery of DNA andex vivotransfection of skin cellsviasaRNA

Gene therapies are undergoing a renaissance, primarily due to their potential for applications in vaccination for infectious diseases and cancers. Although the biology of these technologies is rapidly evolving, delivery strategies need to be improved to overcome the poor pharmacokinetics and cellular transport of nucleic acids whilst maintaining patient safety. In this work, we describe the divergent synthesis of biodegradable cationic dendrimers based on the amino acid ornithine as non-viral gene delivery vectors and evaluate their potential as delivery vectors for DNA and RNA. The dendrimers effectively complexed model nucleic acids at lower N/P ratios than polyethyleneimine and outperformed it in DNA transfection experiments with ratios above 5. Remarkably, all dendrimer polyplexes at N/P = 2 achieved up to 7-fold higher protein content over an optimized PEI formulation when used for transfections with self-amplifying RNA (saRNA). Finally, transfection studies utilizing human skin explants revealed an increase of cells producing protein from 2% with RNA alone to 12% with dendrimer polyplexes, attributed to expression enrichment predominantly in epithelial cells, fibroblasts and leukocytes, with minor enrichment in NK cells, T cells, monocytes, and B cells. Overall, this study indicates the clear potential of ornithine dendrimers as safe and effective delivery vectors for both DNA and RNA therapeutics.

A convenient strategy for synthesizing the Agelas alkaloids clathrodin, oroidin, and hymenidin and their (un)saturated linker analogs

A convenient strategy for the scalable synthesis of the 2-aminoimidazole alkaloids, clathrodin, oroidin, and hymenidin derived from marine Agelas species and their analogs possessing a saturated or unsaturated linker moiety is described. The key intermediates, 4-(3-aminopropyl)-1H-imidazol-2-amine and (E)-4-(3-aminoprop-1-en-1-yl)-1H-imidazol-2-amine were obtained through two different synthetic pathways starting from l-ornithine and benzyl 1,2-dihydropyridine-1-carboxylate respectively, using (i) an innovative combination of Weinreb amide strategy with di-Boc protection, and (ii) a modified pyridine-1(2H)-carboxylate based strategy. Convenient access to these 2-aminoimidazole amines is crucial for the synthesis of libraries of clathrodin, oroidin, and hymenidin analogs.

Staphyloferrin A as siderophore-component in fluoroquinolone-based Trojan horse antibiotics

A series of fluoroquinolone conjugates was synthesised by linking the carboxylic acid functionality of the carboxylate-type siderophore staphyloferrin A and its derivatives to the piperazinyl nitrogen of ciprofloxacin and norfloxacin via amide bond formation. Four siderophore-drug conjugates were screened against a panel of bacteria associated with infection in humans. Whilst no activity was found against ciprofloxacin- or norfloxacin-resistant bacteria, one of the conjugates retained antibacterial activity against fluoroquinolone-susceptible strains although the structure of its lysine-based siderophore component differs from that of the natural siderophore staphyloferrin A. In contrast, three ornithine-based siderophore conjugates showed significantly reduced activity against strains that are susceptible to their respective parent fluoroquinolones, regardless of the type of fluoroquinolone attached or chirality at the ornithine Cα-atom. The loss of potency observed for the (R)- and (S)-ornithine-based ciprofloxacin conjugates correlates with their reduced inhibitory activity against the target enzyme DNA gyrase. The Royal Society of Chemistry.