16937-92-1

Basic information

• Product Name: BOC-D-ORN(Z)-OH
• Synonyms: (R)-12,12-dimethyl-3,10-dioxo-1-phenyl-2,11-dioxa-4,9-diazatridecane-8-carboxylic acid;Boc-N-delta-Cbz-D-ornithine;N^d-Benzyloxycarbonyl-N^a-Boc-D-ornithine, 98%;(R)-5-(((Benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)pentanoic acid;Nα-Boc-Nδ-Z-D-ornithine≥ 99% (HPLC);Ndelta-Benzyloxycarbonyl-Nalpha-Boc-D-ornithine;BOC-D-ORNITHINE(CBZ);BOC-D-ORNITHINE(Z)-OH
• CAS NO: 16937-92-1
• Molecular Formula: C₁₈H₂₆N₂O₆
• Molecular Weight: 366.41
• Product Categories: Ornithine [Org]
• Mol File: 16937-92-1.mol

Chemical Properties

• Boiling Point: 579.1 °C at 760 mmHg
• Flash Point: 304 °C
• Appearance: /Solid
• Density: 1.193 g/cm³
• Vapor Pressure: 2.99E-14mmHg at 25°C
• Refractive Index: 1.526
• Storage Temp.: Store at RT.
• PKA: 3.96±0.21(Predicted)
• BRN: 2400891
• CAS DataBase Reference: BOC-D-ORN(Z)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-D-ORN(Z)-OH(16937-92-1)
• EPA Substance Registry System: BOC-D-ORN(Z)-OH(16937-92-1)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 16937-92-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
BOC-D-ORN(Z)-OH is used as a reagent in peptide chemistry for the synthesis of peptide-based drugs and pharmaceuticals. Its protective groups, BOC and Z, allow for controlled sequence assembly and protection of functional groups during solid-phase peptide synthesis, enhancing the efficiency and specificity of the process.
Used in Organic Chemistry:
BOC-D-ORN(Z)-OH serves as a valuable chemical building block in organic chemistry, facilitating the synthesis of complex organic compounds and contributing to the development of novel therapeutic agents.

InChI:InChI=1/C18H26N2O6/c1-18(2,3)26-17(24)20-14(15(21)22)10-7-11-19-16(23)25-12-13-8-5-4-6-9-13/h4-6,8-9,14H,7,10-12H2,1-3H3,(H,19,23)(H,20,24)(H,21,22)/t14-/m1/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 16937-91-0 N^ε-(benzyloxycarbonyl)ornithine 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 

Downstream Products

• 159877-12-0 (R)-5-amino-2-((tert-butoxycarbonyl)amino)pentanoic acid 
• 352274-96-5 (R)-methyl 2-amino-5-(((benzyloxy)carbonyl)amino)pentanoate 
• 887476-53-1 Boc-(R)-Orn(Z)-OtBu 
• 1044563-65-6 (2R,3R)-benzyl 3-(tert-butoxycarbonylamino)-2-methylpiperidine-1-carboxylate 
• 1044563-67-8 (25,3R)-benzyl 3-(tert-butoxycarbonylamino)-2-methylpiperidine-1-carboxylate 

Relevant articles and documents

Red-fluorescent argininamide-type NPY Y1 receptor antagonists as pharmacological tools

Fluorescently labelled NPY Y1 receptor (Y1R) ligands were synthesized by connecting pyrylium and cyanine dyes with the argininamide-type Y1R antagonist core structure by linkers, covering a wide variety in length and chemical nature, attached to the guanidine group. The most promising fluorescent probes had Y1R affinities (radioligand binding) and antagonistic activities (calcium assay) in the one- to two-digit nanomolar range. These compounds turned out to be stable under assay conditions and to be appropriate for the detection of Y1Rs by confocal microscopy in live cells. To improve the signal-to-noise ratio by shifting the emission into the near infrared, a new benzothiazolium-type fluorescent cyanine dye (UR-DE99) was synthesized and attached to the parent antagonist via a carbamoyl linker yielding UR-MK131, a highly potent fluorescent Y1R probe, which was also successfully applied in flow cytometry.