61280-75-9

Basic information

• Product Name: BOC-D-4-Nitrophe
• Synonyms: BOC-PNO2-D-PHE-OH;BOC-P-NITRO-D-PHENYLALANINE;BOC-P-NITRO-D-PHE-OH;BOC-4-NITRO-D-PHENYLALANINE;BOC-4-NITRO-D-PHE-OH;BOC-D-4-NITROPHE;BOC-D-4-NITROPHENYLALANINE;BOC-D-(P-NO2)PHE-OH
• CAS NO: 61280-75-9
• Molecular Formula: C₁₄H₁₈N₂O₆
• Molecular Weight: 310.3
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Unusual Amino Acids;Boc-Amino acid series
• Mol File: 61280-75-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 120°C
• Boiling Point: 509.3 °C at 760 mmHg
• Flash Point: 261.8 °C
• Appearance: whaite crystalline powder
• Density: 1.29 g/cm³
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol
• PKA: 3.70±0.10(Predicted)
• BRN: 4203814
• CAS DataBase Reference: BOC-D-4-Nitrophe(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-D-4-Nitrophe(61280-75-9)
• EPA Substance Registry System: BOC-D-4-Nitrophe(61280-75-9)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• F: 8
• HazardClass: IRRITANT
• Hazardous Substances Data: 61280-75-9(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

N-Boc-p-nitro-D-phenylalanine is the N-Boc protected form of p-Nitro-D-phenylalanine (N502720). Also a useful synthetic intermediate in the synthesis of (R)-Hydroxymelphalan (H393845, TFA salt); an analog of Melphalan (M216900) which is an antineoplastic.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 56613-61-7 (R)-4-nitro-phenylalanine 
• 673-06-3 D-(R)-phenylalanine 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 

Downstream Products

• 199336-06-6 {(1S,2S)-2-[(R)-2-tert-Butoxycarbonylamino-3-(4-nitro-phenyl)-propionylamino]-cyclohexyl}-carbamic acid benzyl ester 
• 199336-09-9 {(1S,2S)-2-[(R)-2-tert-Butoxycarbonylamino-3-(4-nitro-phenyl)-propionylamino]-cyclohexyl}-carbamic acid tert-butyl ester 
• 199336-08-8 {(1R,2R)-2-[(R)-2-tert-Butoxycarbonylamino-3-(4-nitro-phenyl)-propionylamino]-cyclohexyl}-carbamic acid benzyl ester 
• 176794-96-0 methyl (R)-2-((tert-butoxycarbonyl)amino)-3-(4-nitrophenyl)propanoate 
• 1435265-68-1 N-(N-benzoyl-L-tryptophanyl)-para-nitro-D-phenylalanine methyl ester 
• 1000394-51-3 (S)-2-(4-nitrophenyl)-1-(2-(thiophen-2-yl)thiazol-4-yl)ethan-1-amine hydrobromide 

Relevant articles and documents

Cyclic side-chain-linked opioid analogs utilizing cis- and trans-4-aminocyclohexyl-d-alanine

Cyclization of linear sequences is a well recognized tool in opioid peptide chemistry for generating analogs with improved bioactivities. Cyclization can be achieved through various bridging bonds between peptide ends or side-chains. In our earlier paper we have reported the synthesis and biological activity of a cyclic peptide, Tyr-c[d-Lys-Phe-Phe-Asp]NH2 (1), which can be viewed as an analog of endomorphin-2 (EM-2, Tyr-Pro-Phe-Phe-NH2). Cyclization was achieved through an amide bond between side-chains of d-Lys and Asp residues. Here, to increase rigidity of the cyclic structure, we replaced d-Lys with cis- or trans-4-aminocyclohexyl-d-alanine (d-ACAla). Two sets of analogs incorporating either Tyr or Dmt (2′,6′-dimethyltyrosine) residues in position 1 were synthesized. In the binding studies the analog incorporating Dmt and trans-d-ACAla showed high affinity for both, μ- and δ-opioid receptors (MOR and DOR, respectively) and moderate affinity for the κ-opioid receptor (KOR), while analog with Dmt and cis-d-ACAla was exceptionally MOR-selective. Conformational analyses by NMR and molecular docking studies have been performed to investigate the molecular structural features responsible for the noteworthy MOR selectivity.

Stereochemical influence on the stability of radio-metal complexes in vivo. Synthesis and evaluation of the four stereoisomers of 2-(p- nitrobenzyl)-trans-CyDTPA

Distinct differences in in vivo stability of the two diastereomeric C- Functionalized CyDTPA chelating agents, (CHX-A DTPA and CHX-B DTPA, both racemates), as recently reported prompted further investigation as to why differences in configuration produced striking effects on the in vivo stability of their yttrium complexes. To this end, the four individual component stereoisomers of CHX-A and CHX-B were synthesized and ability to bind yttrium was investigated both in vitro and in vivo.