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Application Area

Nα-Fmoc-Nδ-allyloxycarbonyl-L-ornithine

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category

Fmoc-Amino Acids

Catalog number

BAT-003689

CAS number

147290-11-7

Molecular Formula

C24H26N2O6

Molecular Weight

438.50

Specification
Reference Reading

IUPAC Name

(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-(prop-2-enoxycarbonylamino)pentanoic acid

Synonyms

Fmoc-L-Orn(Aloc)-OH; (S)-2-((((9H-Fluoren-9-Yl)Methoxy)Carbonyl)Amino)-5-(((Allyloxy)Carbonyl)Amino)Pentanoic Acid; N2-Fmoc-N5-Allyloxycarbonyl-L-Ornithine

Appearance

White crystalline powder

Purity

≥ 98% (HPLC)

Density

1.255g/cm3

Melting Point

106-111 °C

Boiling Point

683.9±55.0 °C(Predicted)

Storage

Store at 2-8°C

InChI

InChI=1S/C24H26N2O6/c1-2-14-31-23(29)25-13-7-12-21(22(27)28)26-24(30)32-15-20-18-10-5-3-8-16(18)17-9-4-6-11-19(17)20/h2-6,8-11,20-21H,1,7,12-15H2,(H,25,29)(H,26,30)(H,27,28)/t21-/m0/s1

InChI Key

RXLIOYNXBHZZBI-NRFANRHFSA-N

Canonical SMILES

C=CCOC(=O)NCCCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

1.Pegylated peptides. II. Solid-phase synthesis of amino-, carboxy- and side-chain pegylated peptides.

Lu YA1, Felix AM. Int J Pept Protein Res. 1994 Feb;43(2):127-38.

General procedures are presented for the site-specific pegylation of peptides at the NH2-terminus, side-chain positions (Lys or Asp/Glu) or COOH-terminus using solid-phase Fmoc/tBu methodologies. A model tridecapeptide fragment of interleukin-2, IL-2(44-56)-NH2, was chosen for this study since it possesses several trifunctional amino acids which serve as potential sites for pegylation. The pegylation reagents were designed to contain either Nle or Orn, which served as diagnostic amino acids for confirming the presence of 1 PEG unit per mole of peptide. NH2-Terminal pegylation was carried out by coupling PEG-CH2CO-Nle-OH to the free NH2-terminus of the peptide-resin. Side-chain pegylation of Lys or Asp was achieved by one of two pathways. Direct side-chain pegylation was accomplished by coupling with Fmoc-Lys(PEG-CH2CO-Nle)-OH or Fmoc-Asp(Nle-NH-CH2CH2-PEG)-OH, followed by solid-phase assemblage of the pegylated peptide-resin and TFA cleavage.