104504-45-2,MFCD00051713
Catalog No.:AA003KPV

104504-45-2 | L-4-Benzoylphenylalanine

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Purity
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Price(USD)
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250mg
98%
in stock  
$21.00   $15.00
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1g
98%
in stock  
$25.00   $18.00
- +
5g
98%
in stock  
$122.00   $86.00
- +
10g
98%
in stock  
$242.00   $170.00
- +
  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA003KPV
Chemical Name:
L-4-Benzoylphenylalanine
CAS Number:
104504-45-2
Molecular Formula:
C16H15NO3
Molecular Weight:
269.2952
MDL Number:
MFCD00051713
SMILES:
N[C@H](C(=O)O)Cc1ccc(cc1)C(=O)c1ccccc1
Properties
Properties
 
BP:
467.6°C at 760 mmHg  
Form:
Solid  
Storage:
Inert atmosphere;Room Temperature;  

Computed Properties
 
Complexity:
342  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
5  
XLogP3:
0.2  

Upstream Synthesis Route

[1]Molecules,2013,vol.18,#7,p.8393-8401

[2]Heterocycles,2013,vol.87,#10,p.2119-2126

[1]Heterocycles,2013,vol.87,#10,p.2119-2126

Downstream Synthesis Route

[1]ChemicalCommunications,2006,p.3783-3785

[1]Patent:EP1235851,2006,B1.Locationinpatent:Page/Pagecolumn56

104504-45-2   
N-Acetyl-p-Benzoyl-DL-Phenylalanine 

[1]Patent:US4762881,1988,A

[1]Molecules,2013,vol.18,p.8393-8401

[2]Heterocycles,2013,vol.87,p.2119-2126

Literature

Title: Structure-activity and immunochemical data provide evidence of developmental- and tissue-specific myosuppressin signaling.

Journal: Peptides 20120801

Title: Probing the conformation of the ISWI ATPase domain with genetically encoded photoreactive crosslinkers and mass spectrometry.

Journal: Molecular & cellular proteomics : MCP 20120401

Title: Wide-range protein photo-crosslinking achieved by a genetically encoded N(ε)-(benzyloxycarbonyl)lysine derivative with a diazirinyl moiety.

Journal: Molecular bioSystems 20120401

Title: Caught in the act: covalent cross-linking captures activator-coactivator interactions in vivo.

Journal: ACS chemical biology 20111216

Title: Photoaffinity labeling of Ras converting enzyme using peptide substrates that incorporate benzoylphenylalanine (Bpa) residues: improved labeling and structural implications.

Journal: Bioorganic & medicinal chemistry 20111215

Title: Genetically encoding unnatural amino acids in neural stem cells and optically reporting voltage-sensitive domain changes in differentiated neurons.

Journal: Stem cells (Dayton, Ohio) 20110801

Title: Refinement of glucagon-like peptide 1 docking to its intact receptor using mid-region photolabile probes and molecular modeling.

Journal: The Journal of biological chemistry 20110506

Title: Mapping the ligand-binding site on a G protein-coupled receptor (GPCR) using genetically encoded photocrosslinkers.

Journal: Biochemistry 20110503

Title: Synthetic approach to stop-codon scanning mutagenesis.

Journal: Journal of the American Chemical Society 20110427

Title: Mapping of the SecA·SecY and SecA·SecG interfaces by site-directed in vivo photocross-linking.

Journal: The Journal of biological chemistry 20110408

Title: Identification by photoaffinity labeling of the extracellular N-terminal domain of PAC1 receptor as the major binding site for PACAP.

Journal: Biochimie 20110401

Title: Crystallographic study of a site-specifically cross-linked protein complex with a genetically incorporated photoreactive amino acid.

Journal: Biochemistry 20110118

Title: Temperature dependent photolabeling of the human angiotensin II type 1 receptor reveals insights into its conformational landscape and its activation mechanism.

Journal: Biochemical pharmacology 20101001

Title: Condensed E. coli cultures for highly efficient production of proteins containing unnatural amino acids.

Journal: Bioorganic & medicinal chemistry letters 20101001

Title: A new tool for photoaffinity labeling studies: a partially constrained, benzophenone based, alpha-amino acid.

Journal: Organic & biomolecular chemistry 20100721

Title: The amino-terminus of angiotensin II contacts several ectodomains of the angiotensin II receptor AT1.

Journal: Journal of medicinal chemistry 20100311

Title: Genetic incorporation of unnatural amino acids into proteins in Mycobacterium tuberculosis.

Journal: PloS one 20100101

Title: Biology by design: from top to bottom and back.

Journal: Journal of biomedicine & biotechnology 20100101

Title: Photolabeling identifies transmembrane domain 4 of CXCR4 as a T140 binding site.

Journal: Biochemical pharmacology 20091201

Title: Impact of nonnatural amino acid mutagenesis on the in vivo function and binding modes of a transcriptional activator.

Journal: Journal of the American Chemical Society 20091014

Title: Protein-DNA photo-crosslinking with a genetically encoded benzophenone-containing amino acid.

Journal: Bioorganic & medicinal chemistry letters 20090901

Title: FTIR analysis of GPCR activation using azido probes.

Journal: Nature chemical biology 20090601

Title: Incorporation of the unnatural amino acid p-benzoyl-L-phenylalanine (Bpa) into a G protein-coupled receptor in its native context.

Journal: Advances in experimental medicine and biology 20090101

Title: Residue 17 of sauvagine cross-links to the first transmembrane domain of corticotropin-releasing factor receptor 1 (CRFR1).

Journal: The Journal of biological chemistry 20081219

Title: Identification of ETA and ETB binding domains using ET-derived photoprobes.

Journal: Biochimie 20080601

Title: Unnatural amino acid replacement in a yeast G protein-coupled receptor in its native environment.

Journal: Biochemistry 20080520

Title: Mapping ligand-receptor interfaces: approaching the resolution limit of benzophenone-based photoaffinity scanning.

Journal: Chemical biology & drug design 20080401

Title: Site-specific incorporation of keto amino acids into functional G protein-coupled receptors using unnatural amino acid mutagenesis.

Journal: The Journal of biological chemistry 20080118

Title: Photolabelling the urotensin II receptor reveals distinct agonist- and partial-agonist-binding sites.

Journal: The Biochemical journal 20070215

Title: Structural basis for the recognition of para-benzoyl-L-phenylalanine by evolved aminoacyl-tRNA synthetases.

Journal: Angewandte Chemie (International ed. in English) 20070101

Title: Site-specific incorporation of non-natural amino acids into proteins in mammalian cells with an expanded genetic code.

Journal: Nature protocols 20060101

Title: Photoaffinity cross-linking of the corticotropin-releasing factor receptor type 1 with photoreactive urocortin analogues.

Journal: Biochemistry 20051129

Title: Differential spatial approximation between cholecystokinin residue 30 and receptor residues in active and inactive conformations.

Journal: Molecular pharmacology 20050601

Title: Differential docking of high-affinity peptide ligands to type A and B cholecystokinin receptors demonstrated by photoaffinity labeling.

Journal: Biochemistry 20050503

Title: Photo-cross-linking interacting proteins with a genetically encoded benzophenone.

Journal: Nature methods 20050501

Title: Protein photo-cross-linking in mammalian cells by site-specific incorporation of a photoreactive amino acid.

Journal: Nature methods 20050301

Title: Analysis of ligand-receptor cross-linked fragments by mass spectrometry.

Journal: The journal of peptide research : official journal of the American Peptide Society 20050301

Title: Identification of ligand binding regions of the Saccharomyces cerevisiae alpha-factor pheromone receptor by photoaffinity cross-linking.

Journal: Biochemistry 20041019

Title: Identification of a binding domain of the endothelin-B receptor using a selective IRL-1620-derived photoprobe.

Journal: Biochemistry 20040914

Title: Benzophenone photophore flexibility and proximity: molecular and crystal-state structure of a Bpa-containing trichogin dodecapeptide analogue.

Journal: Chembiochem : a European journal of chemical biology 20040402

Title: Identification of a contact site for residue 19 of parathyroid hormone (PTH) and PTH-related protein analogs in transmembrane domain two of the type 1 PTH receptor.

Journal: Molecular endocrinology (Baltimore, Md.) 20031201

Title: Synthesis of chemotactic peptide analogs with a photoaffinity cross-linker as new probes for analysis of receptor-ligand interaction.

Journal: Protein and peptide letters 20030401

Title: Photolabelling the rat urotensin II/GPR14 receptor identifies a ligand-binding site in the fourth transmembrane domain.

Journal: The Biochemical journal 20030315

Title: Identification of a contact region between the tridecapeptide alpha-factor mating pheromone of Saccharomyces cerevisiae and its G protein-coupled receptor by photoaffinity labeling.

Journal: Biochemistry 20020514

Title: Methionine proximity assay, a novel method for exploring peptide ligand-receptor interaction.

Journal: Journal of receptor and signal transduction research 20020101

Title: Identification of determinants of inverse agonism in a constitutively active parathyroid hormone/parathyroid hormone-related peptide receptor by photoaffinity cross-linking and mutational analysis.

Journal: The Journal of biological chemistry 20011116

Title: Multiple sites of contact between the carboxyl-terminal binding domain of PTHrP-(1--36) analogs and the amino-terminal extracellular domain of the PTH/PTHrP receptor identified by photoaffinity cross-linking.

Journal: The Journal of biological chemistry 20010803

Title: Molecular characterization of the substance P*neurokinin-1 receptor complex: development of an experimentally based model.

Journal: The Journal of biological chemistry 20010622

Title: Tritiated photoactivatable analogs of the native human thrombin receptor (PAR-1) agonist peptide, SFLLRN-NH2.

Journal: The journal of peptide research : official journal of the American Peptide Society 20010601

Title: Photoaffinity labeling of mutant neurokinin-1 receptors reveals additional structural features of the substance P/NK-1 receptor complex.

Journal: Biochemistry 20010227

Title: Mapping tertiary interactions in protein folding reactions: a novel mass spectrometry- and chemical synthesis-based approach.

Journal: Fresenius' journal of analytical chemistry 20010201

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Additional Info:
SDS
Tags:104504-45-2 Molecular Formula|104504-45-2 MDL|104504-45-2 SMILES|104504-45-2 L-4-Benzoylphenylalanine
Catalog No.: AA003KPV
104504-45-2,MFCD00051713
104504-45-2 | L-4-Benzoylphenylalanine
Pack Size: 250mg
Purity: 98%
in stock
$21.00 $15.00
Pack Size: 1g
Purity: 98%
in stock
$25.00 $18.00
Pack Size: 5g
Purity: 98%
in stock
$122.00 $86.00
Pack Size: 10g
Purity: 98%
in stock
$242.00 $170.00
Quantity
- +
Add to Card
Order Now
bulk Quotation Request
Technical Information
Catalog Number: AA003KPV
Chemical Name: L-4-Benzoylphenylalanine
CAS Number: 104504-45-2
Molecular Formula: C16H15NO3
Molecular Weight: 269.2952
MDL Number: MFCD00051713
SMILES: N[C@H](C(=O)O)Cc1ccc(cc1)C(=O)c1ccccc1
Properties
BP: 467.6°C at 760 mmHg  
Form: Solid  
Storage: Inert atmosphere;Room Temperature;  
Complexity: 342  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 1  
Heavy Atom Count: 20  
Hydrogen Bond Acceptor Count: 4  
Hydrogen Bond Donor Count: 2  
Rotatable Bond Count: 5  
XLogP3: 0.2  
Upstream Synthesis Route
63-91-2    98-88-4    104504-45-2 

[1]Molecules,2013,vol.18,#7,p.8393-8401

[2]Heterocycles,2013,vol.87,#10,p.2119-2126

23635-30-5    98-88-4    104504-45-2 

[1]Heterocycles,2013,vol.87,#10,p.2119-2126

Downstream Synthesis Route
51513-80-5    104504-45-2    913987-17-4 

[1]ChemicalCommunications,2006,p.3783-3785

431-47-0    104504-45-2    334616-57-8 

[1]Patent:EP1235851,2006,B1.Locationinpatent:Page/Pagecolumn56

104504-45-2   
N-Acetyl-p-Benzoyl-DL-Phenylalanine 

[1]Patent:US4762881,1988,A

63-91-2    98-88-4    104504-45-2 

[1]Molecules,2013,vol.18,p.8393-8401

[2]Heterocycles,2013,vol.87,p.2119-2126

Literature fold

Title: Structure-activity and immunochemical data provide evidence of developmental- and tissue-specific myosuppressin signaling.

Journal: Peptides20120801

Title: Probing the conformation of the ISWI ATPase domain with genetically encoded photoreactive crosslinkers and mass spectrometry.

Journal: Molecular & cellular proteomics : MCP20120401

Title: Wide-range protein photo-crosslinking achieved by a genetically encoded N(ε)-(benzyloxycarbonyl)lysine derivative with a diazirinyl moiety.

Journal: Molecular bioSystems20120401

Title: Caught in the act: covalent cross-linking captures activator-coactivator interactions in vivo.

Journal: ACS chemical biology20111216

Title: Photoaffinity labeling of Ras converting enzyme using peptide substrates that incorporate benzoylphenylalanine (Bpa) residues: improved labeling and structural implications.

Journal: Bioorganic & medicinal chemistry20111215

Title: Genetically encoding unnatural amino acids in neural stem cells and optically reporting voltage-sensitive domain changes in differentiated neurons.

Journal: Stem cells (Dayton, Ohio)20110801

Title: Refinement of glucagon-like peptide 1 docking to its intact receptor using mid-region photolabile probes and molecular modeling.

Journal: The Journal of biological chemistry20110506

Title: Mapping the ligand-binding site on a G protein-coupled receptor (GPCR) using genetically encoded photocrosslinkers.

Journal: Biochemistry20110503

Title: Synthetic approach to stop-codon scanning mutagenesis.

Journal: Journal of the American Chemical Society20110427

Title: Mapping of the SecA·SecY and SecA·SecG interfaces by site-directed in vivo photocross-linking.

Journal: The Journal of biological chemistry20110408

Title: Identification by photoaffinity labeling of the extracellular N-terminal domain of PAC1 receptor as the major binding site for PACAP.

Journal: Biochimie20110401

Title: Crystallographic study of a site-specifically cross-linked protein complex with a genetically incorporated photoreactive amino acid.

Journal: Biochemistry20110118

Title: Temperature dependent photolabeling of the human angiotensin II type 1 receptor reveals insights into its conformational landscape and its activation mechanism.

Journal: Biochemical pharmacology20101001

Title: Condensed E. coli cultures for highly efficient production of proteins containing unnatural amino acids.

Journal: Bioorganic & medicinal chemistry letters20101001

Title: A new tool for photoaffinity labeling studies: a partially constrained, benzophenone based, alpha-amino acid.

Journal: Organic & biomolecular chemistry20100721

Title: The amino-terminus of angiotensin II contacts several ectodomains of the angiotensin II receptor AT1.

Journal: Journal of medicinal chemistry20100311

Title: Genetic incorporation of unnatural amino acids into proteins in Mycobacterium tuberculosis.

Journal: PloS one20100101

Title: Biology by design: from top to bottom and back.

Journal: Journal of biomedicine & biotechnology20100101

Title: Photolabeling identifies transmembrane domain 4 of CXCR4 as a T140 binding site.

Journal: Biochemical pharmacology20091201

Title: Impact of nonnatural amino acid mutagenesis on the in vivo function and binding modes of a transcriptional activator.

Journal: Journal of the American Chemical Society20091014

Title: Protein-DNA photo-crosslinking with a genetically encoded benzophenone-containing amino acid.

Journal: Bioorganic & medicinal chemistry letters20090901

Title: FTIR analysis of GPCR activation using azido probes.

Journal: Nature chemical biology20090601

Title: Incorporation of the unnatural amino acid p-benzoyl-L-phenylalanine (Bpa) into a G protein-coupled receptor in its native context.

Journal: Advances in experimental medicine and biology20090101

Title: Residue 17 of sauvagine cross-links to the first transmembrane domain of corticotropin-releasing factor receptor 1 (CRFR1).

Journal: The Journal of biological chemistry20081219

Title: Identification of ETA and ETB binding domains using ET-derived photoprobes.

Journal: Biochimie20080601

Title: Unnatural amino acid replacement in a yeast G protein-coupled receptor in its native environment.

Journal: Biochemistry20080520

Title: Mapping ligand-receptor interfaces: approaching the resolution limit of benzophenone-based photoaffinity scanning.

Journal: Chemical biology & drug design20080401

Title: Site-specific incorporation of keto amino acids into functional G protein-coupled receptors using unnatural amino acid mutagenesis.

Journal: The Journal of biological chemistry20080118

Title: Photolabelling the urotensin II receptor reveals distinct agonist- and partial-agonist-binding sites.

Journal: The Biochemical journal20070215

Title: Structural basis for the recognition of para-benzoyl-L-phenylalanine by evolved aminoacyl-tRNA synthetases.

Journal: Angewandte Chemie (International ed. in English)20070101

Title: Site-specific incorporation of non-natural amino acids into proteins in mammalian cells with an expanded genetic code.

Journal: Nature protocols20060101

Title: Photoaffinity cross-linking of the corticotropin-releasing factor receptor type 1 with photoreactive urocortin analogues.

Journal: Biochemistry20051129

Title: Differential spatial approximation between cholecystokinin residue 30 and receptor residues in active and inactive conformations.

Journal: Molecular pharmacology20050601

Title: Differential docking of high-affinity peptide ligands to type A and B cholecystokinin receptors demonstrated by photoaffinity labeling.

Journal: Biochemistry20050503

Title: Photo-cross-linking interacting proteins with a genetically encoded benzophenone.

Journal: Nature methods20050501

Title: Protein photo-cross-linking in mammalian cells by site-specific incorporation of a photoreactive amino acid.

Journal: Nature methods20050301

Title: Analysis of ligand-receptor cross-linked fragments by mass spectrometry.

Journal: The journal of peptide research : official journal of the American Peptide Society20050301

Title: Identification of ligand binding regions of the Saccharomyces cerevisiae alpha-factor pheromone receptor by photoaffinity cross-linking.

Journal: Biochemistry20041019

Title: Identification of a binding domain of the endothelin-B receptor using a selective IRL-1620-derived photoprobe.

Journal: Biochemistry20040914

Title: Benzophenone photophore flexibility and proximity: molecular and crystal-state structure of a Bpa-containing trichogin dodecapeptide analogue.

Journal: Chembiochem : a European journal of chemical biology20040402

Title: Identification of a contact site for residue 19 of parathyroid hormone (PTH) and PTH-related protein analogs in transmembrane domain two of the type 1 PTH receptor.

Journal: Molecular endocrinology (Baltimore, Md.)20031201

Title: Synthesis of chemotactic peptide analogs with a photoaffinity cross-linker as new probes for analysis of receptor-ligand interaction.

Journal: Protein and peptide letters20030401

Title: Photolabelling the rat urotensin II/GPR14 receptor identifies a ligand-binding site in the fourth transmembrane domain.

Journal: The Biochemical journal20030315

Title: Identification of a contact region between the tridecapeptide alpha-factor mating pheromone of Saccharomyces cerevisiae and its G protein-coupled receptor by photoaffinity labeling.

Journal: Biochemistry20020514

Title: Methionine proximity assay, a novel method for exploring peptide ligand-receptor interaction.

Journal: Journal of receptor and signal transduction research20020101

Title: Identification of determinants of inverse agonism in a constitutively active parathyroid hormone/parathyroid hormone-related peptide receptor by photoaffinity cross-linking and mutational analysis.

Journal: The Journal of biological chemistry20011116

Title: Multiple sites of contact between the carboxyl-terminal binding domain of PTHrP-(1--36) analogs and the amino-terminal extracellular domain of the PTH/PTHrP receptor identified by photoaffinity cross-linking.

Journal: The Journal of biological chemistry20010803

Title: Molecular characterization of the substance P*neurokinin-1 receptor complex: development of an experimentally based model.

Journal: The Journal of biological chemistry20010622

Title: Tritiated photoactivatable analogs of the native human thrombin receptor (PAR-1) agonist peptide, SFLLRN-NH2.

Journal: The journal of peptide research : official journal of the American Peptide Society20010601

Title: Photoaffinity labeling of mutant neurokinin-1 receptors reveals additional structural features of the substance P/NK-1 receptor complex.

Journal: Biochemistry20010227

Title: Mapping tertiary interactions in protein folding reactions: a novel mass spectrometry- and chemical synthesis-based approach.

Journal: Fresenius' journal of analytical chemistry20010201

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