N-[(Benzyloxy)carbonyl]-L-phenylalanyl-L-histidyl-L-leucine | CAS No. 28458-19-7

N-[(Benzyloxy)carbonyl]-L-phenylalanyl-L-histidyl-L-leucine

Basic Information

CAS Number

28458-19-7

Molecular Formula

C29H35N5O6

Molecular Weight

549.6 g/mol

AD

Basic Physical Properties

CC(C)CC(C(=O)O)NC(=O)C(CC1=CN=CN1)NC(=O)C(CC2=CC=CC=C2)NC(=O)OCC3=CC=CC=C3

InChI

InChI=1S/C29H35N5O6/c1-19(2)13-25(28(37)38)33-27(36)24(15-22-16-30-18-31-22)32-26(35)23(14-20-9-5-3-6-10-20)34-29(39)40-17-21-11-7-4-8-12-21/h3-12,16,18-19,23-25H,13-15,17H2,1-2H3,(H,30,31)(H,32,35)(H,33,36)(H,34,39)(H,37,38)/t23-,24-,25-/m0/s1

InChIKey

BOMYCHBQXOKSLT-SDHOMARFSA-N

Complexity

828

Synonyms & References

English

  • MFCD00155532
  • Z-Phe-His-Leu
  • Z-PHE-HIS-LEU-OH
  • carbobenzoxy-l-phenylalanyl-l-histidyl-l-leucine
  • (2S)-2-[[(2S)-3-(1H-imidazol-5-yl)-2-[[(2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoyl]amino]-4-methylpentanoic acid
  • SCHEMBL7274809
  • CS-0655363
  • HY-P4594
  • (5S,8S,11S)-8-((1H-imidazol-4-yl)methyl)-5-benzyl-11-isobutyl-3,6,9-trioxo-1-phenyl-2-oxa-4,7,10-triazadodecan-12-oic acid
  • 28458-19-7
  • L-Leucine, N-[(phenylmethoxy)carbonyl]-L-phenylalanyl-L-histidyl-
  • L-Leucine,N-[(phenylmethoxy)carbonyl]-L-phenylalanyl-L-histidyl-
  • Z-L-Phe-L-His-L-Leu-OH
  • Z-phe-his-leu-oh
  • 2-[[2-[(2-benzyloxycarbonylamino-3-phenyl-propanoyl)amino]-3-(1H-imidazol-4-yl)propanoyl]amino]-4-methyl-pentanoic acid

MDL Number

MFCD00155532

FAQ

What are the physical and chemical properties of N-[(Benzyloxy)carbonyl]-L-phenylalanyl-L-histidyl-L-leucine (CAS: 28458-19-7)?

N-[(Benzyloxy)carbonyl]-L-phenylalanyl-L-histidyl-L-leucine (CAS: 28458-19-7) is a crystalline compound with a molecular weight of approximately 594.6 g/mol. It is sparingly soluble in water and has good solubility in organic solvents. The compound is known to be reactive towards hydrolysis and can undergo peptide bond cleavage under certain conditions. Its chemical properties include amide and ester functionalities.

How is N-[(Benzyloxy)carbonyl]-L-phenylalanyl-L-histidyl-L-leucine (CAS: 28458-19-7) typically synthesized?

N-[(Benzyloxy)carbonyl]-L-phenylalanyl-L-histidyl-L-leucine (CAS: 28458-19-7) is synthesized through solid-phase peptide synthesis. Common methods include Fmoc chemistry using a Boc protecting group for side chains. The synthesis involves coupling sequential amino acids with appropriate protecting groups in a solution phase, followed by purification using HPLC. The overall yield is typically around 50-70%, with high purity.

What industries use N-[(Benzyloxy)carbonyl]-L-phenylalanyl-L-histidyl-L-leucine (CAS: 28458-19-7)?

N-[(Benzyloxy)carbonyl]-L-phenylalanyl-L-histidyl-L-leucine (CAS: 28458-19-7) is primarily used in the pharmaceutical industry for the development of peptide drugs. It is also utilized in research for peptide synthesis, drug discovery, and as a model compound for studying peptide-protein interactions. Additionally, this compound may be used in the production of certain sensors and in polymer chemistry for specific applications.

What precautions should be taken when handling N-[(Benzyloxy)carbonyl]-L-phenylalanyl-L-histidyl-L-leucine (CAS: 28458-19-7)?

When handling N-[(Benzyloxy)carbonyl]-L-phenylalanyl-L-histidyl-L-leucine (CAS: 28458-19-7), use appropriate personal protective equipment (PPE) such as gloves, safety goggles, and a lab coat. Work in a well-ventilated area or a fume hood to avoid inhalation of dust or vapors. Store the compound in a cool, dry place away from direct sunlight and flammable materials. In case of spill, immediately clean up according to the Material Safety Data Sheet (MSDS). Always refer to the latest SDS for detailed safety information.

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