Nα,δ-Bis-Boc-D-ornithine - CAS 137524-82-4

BOC-Amino Acids
Catalog number
CAS number
Molecular Formula
Molecular Weight
Boc-D-Orn(Boc)-OH; 2,5-bis[[(2-methylpropan-2-yl)oxy-oxomethyl]amino]pentanoic acid; N,N'-Bis-Boc-D-ornithine
≥ 99%
Melting Point
117-123 °C
Boiling Point
504.1 °C at 760 mmHg
Store at 2-8 °C
InChI Key
Canonical SMILES
1.Cyclic morphiceptin analogs: cyclization studies and opioid activities in vitro.
Vogel D1, Schmidt R, Hartung K, Demuth HU, Chung NN, Schiller PW. Int J Pept Protein Res. 1996 Dec;48(6):495-502.
Attempts were undertaken to develop cyclic beta-casomorphin-5 analogs with improved opioid activity profiles by deletion of the glycine residue in position 5, leading to analogs structurally related to the opioid peptide morphiceptin (H-Tyr-Pro-Phe-Pro-NH2). The tetrapeptide sequence Boc-Tyr(tBu)-D-Xaa-Phe-Yaa-OH (Xaa = Lys, Orn, A2bu; Yaa = Pro in L- or D-configuration) was used to study the influence of ring size and chirality on the yield of cyclization between the omega-amino group of Xaa and the C-terminal carboxyl group. In all cases the cyclization reaction was performed under identical experimental conditions to allow a direct comparison with regard to yield and homogeneity. The reaction products were purified by crystallization and liquid chromatography, and were characterized by HPLC, TLC, electrospray mass spectrometry and 1H-NMR spectroscopy. In none of the reactions performed with the cyclization precursors containing proline in the L-configuration could a cyclic monomer be detected, and the cyclodimer (7-9) was the exclusive product in each case.
2.Solid-Phase Total Synthesis of Bacitracin A.
Lee J1, Griffin JH, Nicas TI. J Org Chem. 1996 Jun 14;61(12):3983-3986.
An efficient solid-phase method for the total synthesis of bacitracin A is reported. This work was undertaken in order to provide a general means of probing the intriguing mode of action of the bacitracins and exploring their potential for use against emerging drug-resistant pathogens. The synthetic approach to bacitracin A involves three key features: (1) linkage to the solid support through the side chain of the L-asparaginyl residue at position 12 (L-Asn(12)), (2) cyclization through amide bond formation between the alpha-carboxyl of L-Asn(12) and the side chain amino group of L-Lys(8), and (3) postcyclization addition of the N-terminal thiazoline dipeptide as a single unit. To initiate the synthesis, Fmoc L-Asp(OH)-OAllyl was attached to a PAL resin. The chain of bacitracin A was elaborated in the C-to-N direction by sequential piperidine deprotection/HBTU-mediated coupling cycles with Fmoc D-Asp(OtBu)-OH, Fmoc L-His(Trt)-OH, Fmoc D-Phe-OH, Fmoc L-Ile-OH, Fmoc D-Orn(Boc)-OH, Fmoc L-Lys(Aloc)-OH, Fmoc L-Ile-OH, Fmoc D-Glu(OtBu)-OH, and Fmoc L-Leu-OH.
3.The new esters derivatives of betulin and betulinic acid in epidermoid squamous carcinoma treatment - In vitro studies.
Drąg-Zalesińska M1, Wysocka T1, Borska S1, Drąg M2, Poręba M2, Choromańska A3, Kulbacka J4, Saczko J3. Biomed Pharmacother. 2015 May;72:91-7. doi: 10.1016/j.biopha.2015.04.003. Epub 2015 Apr 13.
BACKGROUND: Betulinic acid and betulin are triterpenes with documented cytotoxic properties toward various cell lines. Unfortunately both betulinic acid and its metabolic precursor, betulin, are very poorly soluble in aqueous buffers, thus their bioavailability and bio-distribution are insufficient in terms of medical applications.
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