147071-84-9

Basic information

• Product Name: H-ORN(FMOC)-OH
• Synonyms: ORNITHINE(FMOC)-OH;N-DELTA-(9-FLUORENYLMETHOXYCARBONYL)-L-ORNITHINE;N-DELTA-FMOC-L-ORNITHINE;H-ORN(FMOC)-OH;L-Ornithine, N5-[(9H-fluoren-9-ylMethoxy)carbonyl]-;N^d-FMoc-L-ornithine, 95%;L-Orn(Fmoc)-OH;Nδ-Fmoc-L-ornithine≥ 99% (HPLC)
• CAS NO: 147071-84-9
• Molecular Formula: C20H22N2O4
• Molecular Weight: 354.4
• Mol File: 147071-84-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 151-153 °C
• Boiling Point: 603.8±55.0 °C(Predicted)
• Appearance: /
• Density: 1.268±0.06 g/cm3(Predicted)
• Storage Temp.: Store at RT.
• PKA: 2.51±0.24(Predicted)
• CAS DataBase Reference: H-ORN(FMOC)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: H-ORN(FMOC)-OH(147071-84-9)
• EPA Substance Registry System: H-ORN(FMOC)-OH(147071-84-9)

Safety Data

• Hazardous Substances Data: 147071-84-9(Hazardous Substances Data)

Usage

General Description

H-ORN(FMOC)-OH, also known as Fmoc-L-Ornithine or Fmoc-Orn-OH, is a common reagent used in organic synthesis and peptide research. The "FMOC" part stands for 9-fluorenylmethoxycarbonyl, a protective group often used in the synthesis of peptides. It protects the amino group of the amino acid ornithine during the formation of peptide bonds. The abbreviation H-ORN stands for the amino acid L-ornithine, which is a key compound in the urea cycle and plays roles in various metabolic processes. "OH" indicates the presence of a hydroxyl group. Overall, H-ORN(FMOC)-OH is a critical building block in peptide synthesis, aiding in the creation of complex bioactive peptides.

Upstream product

• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 3184-13-2 L-ornithine hydrochloride 
• 70-26-8 L-ornithine 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 

Relevant articles and documents

Decomposition of copper-amino acid complexes by oxalic acid dihydrate

A facile approach to the synthesis of some side-chain-protected amino acids via oxalic acid dihydrate as the copper sequestering reagent is presented. The copper in the amino acid complex reacted with oxalic acid dihydrate to form insoluble cupric oxalate, with the free amino acid released. Compared with conventional methods, this method is convenient, inexpensive, and environmentally friendly.

Epimerization of peptide nucleic acids analogs during solid-phase synthesis: Optimization of the coupling conditions for increasing the optical purity

Peptide nucleic acid (PNA) analogs based on Nα-(thymin-1-ylacetyl)ornithine were previously shown to form triplexes with complementary RNA. In order to obtain optically pure compounds for hybridization experiments, chiral monomers based on D- or L-ornithine, Nδ-Fmoc-Nα-(thymin-1-ylacetyl)ornithine 2 and Nδ-Fmoc-Nα (uracil-1-ylacetyl)ornithine 3 were synthesized either by a one-step or by a simple three-step procedure starting from Nδ-protected ornithine; the latter procedure led to enantiomerically pure products. Oligomerization of 2 and 3 was carried out either in solution, or by solid-phase peptide synthesis (SPPS) on an MBHA-Rink amide resin. The oligomers turned out to contain large amounts of epimerization products, especially those obtained by SPPS. Therefore, we examined carefully the parameters which may be involved in epimerization: the nature of the coupling reagent, of the base, and the addition mode. Coupling of the monomer L-3 was performed under various conditions. Lower racemization was found to occur when using (7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU) as coupling agent and 2,4,6-trimethylpyridine (sym-collidine, TMP) as base, without preactivation, leading to a residual 4% of the D-enantiomer. By applying a procedure based on the stepwise addition of the base the D-enantiomer content was reduced to less than 1%. Using this procedure, a decamer of L-3 was synthesized, which was shown to contain less than 2% of the D-ornithine derivative.