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Chemical Structure| 27219-07-4 Chemical Structure| 27219-07-4
Chemical Structure| 27219-07-4

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Boc-NH-C4-acid is a compound with a Boc-protected amine group and a four-carbon chain, often used in peptide synthesis and organic reactions.

Synonyms: 5-Boc-amino-pentanoic acid; Boc-5-aminovaleric acid; Boc-5-aminopentanoic acid

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Product Details of Boc-NH-C4-acid

CAS No. :27219-07-4
Formula : C10H19NO4
M.W : 217.26
SMILES Code : CC(C)(C)OC(=O)NCCCCC(O)=O
Synonyms :
5-Boc-amino-pentanoic acid; Boc-5-aminovaleric acid; Boc-5-aminopentanoic acid
MDL No. :MFCD00076903
InChI Key :GFMRZAMDGJIWRB-UHFFFAOYSA-N
Pubchem ID :545848

Safety of Boc-NH-C4-acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Boc-NH-C4-acid

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 27219-07-4 ]

[ 27219-07-4 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 27219-07-4 ]
  • [ 124-41-4 ]
  • [ 3034-48-8 ]
  • [ 1235447-16-1 ]
  • 2
  • [ 27219-07-4 ]
  • Fmoc-Ser(octyl)-OH [ No CAS ]
  • [ 103478-62-2 ]
  • [ 77128-73-5 ]
  • [N-aminopentanoyl-Ser3(octyl)-(Me)Phe4-(Me)Leu5]-ghrelin(3-5)-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Fmoc-amide resin (0.40 g, 0.25 mmol) was placed in a reaction vessel equipped with a glass filter, and 15 mL of 20percent piperidine in NMP was added thereto and shaken for 20 minutes, thus removing the Fmoc group. Thereafter, 15 mL NMP, 1.0 mmol (4 equivalents) of Fmoc-MeLeu-OH, 1.0 mmol (4 equivalents) of TBTU, 1.0 mmol (4 equivalents) of HOBt and 1.0 mmol (4 equivalents) of DIPEA were added thereto and shaken for 1 hour to condense the Fmoc-MeLeu. Thereafter, the peptide chain was extended by repeatedly carrying out removal of Fmoc group by 20percent piperidine and condensation of Fmoc-amino acid (3 equivalents) by bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (3 equivalents) in the presence of 2.25 mmol (9 equivalents) of DIPEA. The conclusion of the condensation reaction was confirmed by deprotecting a small amount of the resin with TFA and examining it by HPLC and mass spectrometry (MS). After Boc-NH?(CH2)4?CO-Ser (O?C8H17)-MePhe-MeLeu-resin was obtained, this resin was treated with TFA for 30 minutes, whereby the resin was cleaved to de-protect the peptide. After the TFA was evaporated, the peptide was washed with ether (Et2O) to give 120 mg NH2?(CH2)4?CO-Ser(C8H17)-MePhe-MeLeu-NH2. This product was applied to YMC-Pack ODS-A (C18, 20 mm×250 mm) and eluted with a linear gradient (flow rate: 10 mL/min.) for 60 minutes of 0 to 54percent acetonitrile in 0.1percent trifluoroacetic acid. The desired fractions were collected and lyophilized to give 70 mg of the desired product. After this derivative was hydrolyzed with propionic acid-HCl (50/50) at 150° C. for 2 hours, the amount of the peptide was quantified using the ratio of the peak area of aminopentanoic acid detected in the amino acid analyzer to that of 10 nmol aminopentanoic acid as a standard. ESI-MS [M+H]; 604.5 (theoretical: 603.8), detected amino acids after hydrolysis with propionic acid?HCl (50/50) at 150° C. for 2 hours: Ser, Ape.
 

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