Fmoc-Orn(Boc)-OH is a protected ornithine derivative with the amino group protected by 9-fluorenylmethoxycarbonyl (Fmoc) and the side-chain amino group protected by tert-butoxycarbonyl (Boc), suitable for peptide synthesis.

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Quality Control of Fmoc-Orn(Boc)-OH Purity: 97% SDS Specification

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Product Citations

Cationic Peptides and Their Cu(II) and Ni(II) Complexes: Coordination and Biological Characteristics

Kotynia, Aleksandra ; Wiatrak, Benita ; Kamysz, Wojciech ; Neubauer, Damian ; Jawien, Paulina ; Marciniak, Aleksandra

DOI: 10.3390/ijms222112028 PubMed ID: 34769458 Int. J. Mol. Sci.,2021,22(21):12028.

Abstract: Antimicrobial peptides are a promising group of compounds used for the treatment of infections. In some cases, metal ions are essential to activate these mols. Examples of metalloantibiotics are, for instance, bleomycin and dermcidin. This study is focused on three new pseudopeptides with potential biol. activity. The coordination behavior of all ligands with Cu(II) and Ni(II) ions has been examined Various anal. methods such as potentiometric titration, UV-Vis and CD spectroscopies, and mass spectrometry were used. All compounds are convenient chelators for metal ion-binding. Two of the ligands tested have histidine residues. Surprisingly, imidazole nitrogen is not involved in the coordination of the metal ion. The N-terminal amino group, Dab side chains, and amide nitrogen atoms of the peptide bonds coordinated Cu(II) and Ni(II) in all the complexes formed. The cytotoxicity of three pseudopeptides and their complexes was evaluated. Moreover, their other model allowed for assessing the attenuation of LPS-induced cytotoxicity and anti-inflammatory activities were also evaluated, the results of which revealed to be very promising.

Keywords: Cu(II) complexes ; LPS-neutralization ; Ni(II) complexes ; anti-inflammatory ; cationic peptides ; potentiometric titration ; spectroscopic methods

Purchased from AmBeed: 109425-55-0

Product Details of Fmoc-Orn(Boc)-OH

CAS No. :	109425-55-0
Formula :	C₂₅H₃₀N₂O₆
M.W :	454.52
SMILES Code :	O=C(O)[C@H](CCCNC(OC(C)(C)C)=O)NC(OCC1C2=CC=CC=C2C3=CC=CC=C13)=O
MDL No. :	MFCD00065668
InChI Key :	JOOIZTMAHNLNHE-NRFANRHFSA-N
Pubchem ID :	2756114

Safety of Fmoc-Orn(Boc)-OH

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of Fmoc-Orn(Boc)-OH

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 109425-55-0 ]

[ 109425-55-0 ] Synthesis Path-Downstream 1~30

1
[ 71989-31-6 ]
[ 108-24-7 ]
[ 77128-73-5 ]
[ 109425-55-0 ]
FMOC-D-Cha-OH [ No CAS ]
Fmoc-L-Arg(pbf)-Wang resin [ No CAS ]
Ac-Phe-Orn-Pro-dCha-(N-Me-Phe)-Arg-OH [ No CAS ]

References: [1]Molecular Pharmacology,2004,vol. 65,p. 868 - 879.

2
2-chlorotrityl chloride polystyrene resin [ No CAS ]
[ 162502-65-0 ]
[ 27144-18-9 ]
[ 29022-11-5 ]
[ 71989-31-6 ]
[ 71989-23-6 ]
[ 71989-35-0 ]
[ 132388-59-1 ]
[ 86060-81-3 ]
[ 109425-55-0 ]
C₉₃H₁₁₆N₁₁O₁₆PolS₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Synthesis of the peptide is carried out by a regular stepwise Fmoc SPPS procedure starting from 2-Cl-Trt-chloride resin. The first amino acid (Fmoc-Gly) is loaded on the resin as described in previous examples to obtain a loading of about 0.7 mmol/g of amino acid/resin. After washing of the resin and removal of the Fmoc group by treatment with piperidine/DMF, the second amino acid (Fmoc-Orn(Boc)) is introduced to continue sequence elongation. Fmoc protected amino acids are activated in situ using TBTU/HOBt and subsequently coupled to the resin over about 50 minutes. Diisopropylethylamine or collidine is used during coupling as an organic base. Completion of the coupling is indicated by ninhydrin test. After washing of the resin, the Fmoc protecting group on the alpha-amine is removed with 20% piperidine in DMF for 20 min. These steps are repeated each time with another amino acid according to the peptide sequence. All amino acids used are Fmoc-Nalpha protected. Trifunctional amino acids are side chain protected as follows: Cys(Acm), Thr(tBu), Asn(Trt), and Orn(Boc). Three equivalents of the activated amino acids are used in the coupling reactions. At the end of the synthesis, the peptide-resin is washed with DMF, followed by DCM, and dried under vacuum to obtain dry peptide-resin.

References: [1]Patent: US2006/276626,2006,A1 .Location in patent: Page/Page column 22.

3
[ 68858-20-8 ]
[ 35661-40-6 ]
[ 71989-38-3 ]
[ 103213-32-7 ]
[ 109425-55-0 ]
[ 96402-49-2 ]
1-tert-butoxycarbonyl-N-[(9-fluorenyl)methoxycarbonyl]-D-tryptophan [ No CAS ]
Fmoc-S-trityl penicillamine [ No CAS ]
C₆₀H₇₄N₁₀O₁₀S₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 3927 - 3940.

4
[ 68858-20-8 ]
[ 35661-40-6 ]
[ 71989-38-3 ]
[ 103213-32-7 ]
[ 109425-55-0 ]
[ 95753-55-2 ]
1-tert-butoxycarbonyl-N-[(9-fluorenyl)methoxycarbonyl]-D-tryptophan [ No CAS ]
Fmoc-S-trityl penicillamine [ No CAS ]
C₅₆H₇₁N₁₁O₁₂S₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 3927 - 3940.

5
[ 353491-47-1 ]
[ 67-56-1 ]
[ 1730-89-8 ]
[ 178924-05-5 ]
[ 68858-20-8 ]
[ 118904-37-3 ]
[ 71989-35-0 ]
[ 109425-55-0 ]
[ 71989-31-6 ]
[ 84624-17-9 ]
(4S)-MeHex-D-Val-Thr(tBu)-Val-D-Val-D-Pro-Orn(Boc)-D-aIle-D-Dpr(H-Phe-(Z)Dhb-Val)(Me)-D-aIle-D-Val-OH [ No CAS ]

References: [1]European Journal of Organic Chemistry,2010,p. 2536 - 2543.

6
[ 353491-47-1 ]
[ 1730-89-8 ]
[ 178924-05-5 ]
[ 68858-20-8 ]
[ 118904-37-3 ]
[ 71989-35-0 ]
[ 109425-55-0 ]
[ 71989-31-6 ]
[ 84624-17-9 ]
(4S)-MeHex-D-Val-Thr(tBu)-Val-D-Val-D-Pro-Orn(Boc)-D-aIle-D-Dpr(H-Phe-(Z)Dhb-Val)-D-aIle-D-Val-OH [ No CAS ]

References: [1]European Journal of Organic Chemistry,2010,p. 2536 - 2543.

7
[ 1730-89-8 ]
[ 178924-05-5 ]
[ 68858-20-8 ]
[ 118904-37-3 ]
[ 71989-35-0 ]
[ 109425-55-0 ]
[ 71989-31-6 ]
[ 84624-17-9 ]
(4S)-MeHex-D-Val-Thr(tBu)-Val-D-Val-D-Pro-Orn(Boc)-D-aIle-D-Dpr-D-aIle-D-Val-OH [ No CAS ]

References: [1]European Journal of Organic Chemistry,2010,p. 2536 - 2543.

8
Fmoc-His(1-Bzl)-OH [ No CAS ]
[ 268734-27-6 ]
[ 71989-23-6 ]
[ 86123-10-6 ]
[ 109425-55-0 ]
[ 1213772-61-2 ]