2274-58-0

Basic information

• Product Name: Z-ORN(Z)-OH
• Synonyms: N-ALPHA, N-DELTA-DIBENZYLOXYCARBONYL-L-ORNITHINE;N-ALPHA,N-DELTA-DICARBOBENZOXY-L-ORNITHINE;N-ALPHA,N-DELTA-DI-CBZ-L-ORNITHINE;N-ALPHA, N-DELTA-BIS(BENZYLOXYCARBONYL)-L-ORNITHINE;N-ALPHA,DELTA-BIS-Z-L-ORNITHINE;Z-L-ORN(Z)-OH;Z-ORNITHINE(Z)-OH;Z-ORN(Z)-OH
• CAS NO: 2274-58-0
• Molecular Formula: C₂₁H₂₄N₂O₆
• Molecular Weight: 400.43
• EINECS: 218-889-0
• Product Categories: Amino Acid Derivatives
• Mol File: 2274-58-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 653.3 °C at 760 mmHg
• Flash Point: 348.9 °C
• Appearance: /
• Density: 1.258
• Storage Temp.: Store at RT.
• PKA: 3.94±0.21(Predicted)
• CAS DataBase Reference: Z-ORN(Z)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-ORN(Z)-OH(2274-58-0)
• EPA Substance Registry System: Z-ORN(Z)-OH(2274-58-0)

Safety Data

• Hazardous Substances Data: 2274-58-0(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Upstream product

• 16682-12-5 D-ornithine hydrochloride 
• 501-53-1 benzyl chloroformate 
• 70-26-8 D-ornithine 
• 3184-13-2 L-ornithine hydrochloride 
• 70-26-8 L-ornithine 

Downstream Products

• 57133-27-4 (S)-N,N-dibenzyloxycarbonyl-β-lysine methyl ester 
• 60242-84-4 (R)-N,N-dibenzyloxycarbonyl-β-lysine methyl ester 
• 4818-10-4 N-(N^α.N^δ-bis-benzyloxycarbonyl-L-ornithyl)-L-leucine methyl ester 
• 731862-29-6 methyl (S)-2,5-bis(((benzyloxy)carbonyl)amino)pentanoate 
• 881837-57-6 benzyl ((4S)-5-[(3-amino-2-hydroxypropyl)amino]-4-{[(benzyloxy)carbonyl]amino}-5-oxopentyl)carbamate hydrochloride 
• 919988-58-2 benzyl [(1S)-4-{[(benzyloxy)carbonyl]amino}-1-({[3-({[(8S,11S,14S)-14-[(tert-butoxycarbonyl)amino]-11-{3-[(tert-butoxycarbonyl)amino]propyl}-17-hydroxy-10,13-dioxo-9,12-diazatricyclo[14.3.1.12,6]henicosa-1⁽²⁰⁾,2⁽²¹⁾,3,5,16,18-hexaen-8-yl]acetyl}amino)-2-hydroxypropyl]amino}carbonyl)butyl]carbamate 
• 73870-98-1 α,δ-Di-Z-L-Orn-L-Leu-D-Phe-OMe 
• 106802-64-6 N,N'-Bis-(N,N'-di-benzyloxycarbonyl-L-ornithyl)-hexamethylendiamin 

Relevant articles and documents

CONJUGATES COMPRISING SELF-IMMOLATIVE GROUPS AND METHODS RELATED THERETO

In some aspects, the invention relates to an antibody-drug conjugate, comprising an antibody; a linker; and an active agent. The antibody-drug conjugate may comprise a self- immolative group. The linker may comprise an O-substituted oxime, e.g., wherein the oxygen atom of the oxime is substituted with a group that covalently links the oxime to the active agent; and the carbon atom of the oxime is substituted with a group that covalently links the oxime to the antibody.

Stereoselective approach to cis -2,3-disubstituted piperidines via reduction of N -acyliminium ion intermediate: Enantioselective synthesis of (+)-(2 S,3 S)-CP-99,994

A very simple and efficient stereoselective approach to cis-2,3-disubstituted piperidines via the reduction of N-acyliminium ion intermediates is described. Application of this methodology is exemplified by the enantioselective total synthesis of (+)-(2S,3S)-CP-99,994.

Differentiation Among the Four Diastereomers of Benzyloxycarbonyl-protected γ-Hydroxyornithine in Negative-ion Fast Atom Bombardment Mass Spectrometry

Discrimination among the four γ-hydroxyornithine diastereomers was studied by fast atom bombardment mass spectrometry (FABMS).It is impossible to distinguish among the four diastereomers of this amino acid by positive- and negative-ion FAB and collisionally activated dissociation MS, but benzyloxycarbonyl group protection of the α- and δ-amino groups in γ-hydroxyornithine allows differentiation among the diastereomers in negative-ion FABMS.The negative-ion mass spectra of benzyloxycarbonyl-protected γ-hydroxyornithine diastereomers showed differences among the abundances of the molecule ion (-), the dehydrated ion (-) due to the loss of the γ-hydroxyl group and the fragment ions formed from both (-) and (-) ions.On the other hand, no difference was found between the fragmentations of the benzyloxycarbonyl-protected enantiomers of ornithine in negative-ion FABMS.These results indicate that the orientation of the γ-hydroxyl group and the existence of two benzene rings in the benzyloxycarbonyl group are important factors which are responsible for the fragmentations of the four benzyloxycarbonyl-protected γ-hydroxyornithine diastereomers in negative-ion FABMS.These studies also showed that the negative-ion FABMS for benzyloxycarbonyl-protected γ-hydroxyornithine diastereomers is a useful method for determining the configuration of each diastereomer of γ-hydroxyornithine.