Nδ-Boc-L-ornithine
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Nδ-Boc-L-ornithine

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Category
BOC-Amino Acids
Catalog number
BAT-002992
CAS number
13650-49-2
Molecular Formula
C10H20N2O4
Molecular Weight
232.30
Nδ-Boc-L-ornithine
IUPAC Name
(2S)-2-amino-5-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid
Synonyms
L-Orn(Boc)-OH; (S)-2-Amino-5-((Tert-Butoxycarbonyl)Amino)Pentanoic Acid
Appearance
White to off-white powder
Purity
≥ 98% (HPLC)
Density
1.135 g/cm3
Boiling Point
401.5°C
Storage
Store at 2-8 °C
InChI
InChI=1S/C10H20N2O4/c1-10(2,3)16-9(15)12-6-4-5-7(11)8(13)14/h7H,4-6,11H2,1-3H3,(H,12,15)(H,13,14)/t7-/m0/s1
InChI Key
GLZZMUULAVZVTA-ZETCQYMHSA-N
Canonical SMILES
CC(C)(C)OC(=O)NCCCC(C(=O)O)N
1.Synthesis of a hydroxyethylene isostere of the tripeptide Arg-Gly-Leu via a convergent acyl-like radical addition strategy.
Jensen CM1, Lindsay KB, Andreasen P, Skrydstrup T. J Org Chem. 2005 Sep 16;70(19):7512-9.
[reaction: see text] A hydroxyethylene isostere of the tripeptide Arg-Gly-Leu, representing an important fragment of a novel cyclic-peptide-based uPA inhibitor, was synthesized in few steps employing as the key step a samarium diiodide promoted coupling of either the 4-thiopyridyl ester of N(alpha)-Fmoc- or N(alpha)-Cbz-protected L-ornithine with the N-acryloyl derivative of L-leucine methyl ester. Epimerization under the coupling conditions at the chiral center in the alpha-position to the ketone was demonstrated not to take place. A stereoselective reduction of the Cbz-protected aminoketone obtained from this radical reaction was promoted by the same single-electron reducing agent in the presence of methanol providing the syn-amino alcohol with a diastereoselectivity of 85:15. With the use of lithium tri-tert-butoxyaluminum hydride in methanol, the corresponding anti-isomer was obtained almost exclusively. Subsequent elaboration of the ornithine moiety in the anti-isomer by introduction of the guanidine group followed by hydrolysis of the C-terminal ester bond and protection of the alcohol as its tert-butyldimethylsilyl ether provided the desired tripeptide mimic.
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