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Application Area

Nα,δ-Bis-Boc-L-ornithine

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

Category

BOC-Amino Acids

Catalog number

BAT-002911

CAS number

57133-29-6

Molecular Formula

C15H28N2O6

Molecular Weight

332.40

Specification
Reference Reading

IUPAC Name

(2S)-2,5-bis[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid

Synonyms

Boc-L-Orn(Boc)-OH; (2S)-2,5-bis[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid; N,N'-Bis-Boc-L-ornithine

Purity

≥ 98% (HPLC)

Density

1.123±0.06 g/cm3

Melting Point

117-124 °C

Boiling Point

504.1±45.0 °C

Storage

Store at 2-8 °C

InChI

InChI=1S/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)/t10-/m0/s1

InChI Key

RJOJSMIZZYHNQG-JTQLQIEISA-N

Canonical SMILES

CC(C)(C)OC(=O)NCCCC(C(=O)O)NC(=O)OC(C)(C)C

1.An unnatural amino acid that induces beta-sheet folding and interaction in peptides.

Nowick JS1, Lam KS, Khasanova TV, Kemnitzer WE, Maitra S, Mee HT, Liu R. J Am Chem Soc. 2002 May 8;124(18):4972-3.

This paper introduces a unique amino acid that can readily be incorporated into peptides to make them fold into beta-sheetlike structures that dimerize through beta-sheet interactions. This new amino acid, Orn(i-PrCO-Hao), consists of an ornithine residue with the beta-strand-mimicking amino acid Hao [J. Am. Chem. Soc. 2000, 122, 7654-7661] attached to its side chain. When Orn(i-PrCO-Hao) is incorporated into a peptide, or appended to its N-terminus, the Hao group hydrogen bonds to the three subsequent residues to form a beta-sheetlike structure. The amino acid Orn(i-PrCO-Hao) is readily used in peptide synthesis as its Fmoc derivative, Fmoc-Orn(i-PrCO-Hao)-OH (3). Fmoc-Orn(i-PrCO-Hao)-OH behaves like a regular amino acid in peptide synthesis and was uneventfully incorporated into the peptide o-anisoyl-Val-Orn(i-PrCO-Hao)-Phe-Ile-Leu-NHMe (4) through standard automated Fmoc solid-phase peptide synthesis, with DIC and HOAt as the coupling agent for Fmoc-Orn(i-PrCO-Hao)-OH and o-anisic acid and HATU as the coupling agent for all other couplings.