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Home > Encyclopedia > Fmoc-3-(4-pyridyl)-L-alanine

Fmoc-3-(4-pyridyl)-L-alanine

Fmoc-3-(4-pyridyl)-L-alanine structure

Fmoc-3-(4-pyridyl)-L-alanine 

structure
  • CAS No:

    169555-95-7

  • Formula:

    C23H20N2O4

  • Chemical Name:

    Fmoc-3-(4-pyridyl)-L-alanine

  • Synonyms:

    FMOC-(S)-2-AMINO-3-(4'-PYRIDYL)PROPANOIC ACID;FMOC-L-4PAL-OH;FMOC-L-4-PYRIDYLALANINE;FMOC-L-4-PAL;FMOC-BETA-(4-PYRIDYL)-L-ALANINE;Fmoc-beta-(4-pyridyl)-Ala-OH;Fmoc-L-4-Pyridylala;Fmoc-L-3-(4-Pyridyl)-alanine

  • Categories:

    Biochemical Engineering  >  Amino Acids and Derivatives

Description

Light yellow powder

Fmoc-3-(4-pyridyl)-L-alanine Basic Attributes

388.42

388.142303

DTXSID10359652

29333990

Characteristics

88.5

3.6

1.309±0.06 g/cm3(Predicted)

646.9±55.0 °C(Predicted)

345.0±31.5 °C

1.637

Soluble in 0.1g in 4mL DMF(clearly soluble).

2-8°C

1.28E-17mmHg at 25°C

Safety Information

IRRITANT

NONH for all modes of transport

3

24/25

Xi

P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

H315

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Fmoc-3-(4-pyridyl)-L-alanine Use and Manufacturing

General procedure: Peptides were synthesized using a solid phase peptide synthesis protocol using an Aapptec FocusXC automated peptide synthesizer coupled with a heating system using the Fmoc chemistry andWang resin as solid support [34]. To prepare the resin for synthesis, a reaction vessel equipped with asintered glass bottom was charged with Fmoc-Leu-Wang resin (0.2 mM), and swelled in a mixture ofdichloromethane and DMF (1:1) for 15 min. The resin was then transferred to a peptide synthesizerreaction vessel. The resin was deprotected twice using 20% piperidine in DMF for 5 min at 70 C.Subsequently, an Fmoc-protected amino acid was double coupled with the Leucine-wang resin bytreating with N, N'-diisopropylcarbodiimide (3.0 equiv., 0.2 M in DMF) and Oxyma (3.0 equiv., 0.2 M inDMF) at 70 C for 8 min. Completion of coupling reactions was monitored by a Kaiser's test for theinitial peptide [40]. Each coupling was followed by removal of the Fmoc group using 20% piperidinein DMF at 70 C for 5 min and repeated once. The cycle of the Fmoc removal and coupling wasrepeated with subsequent Fmoc-protected amino acids to generate the desired resin-bound peptide.Cleavage of the peptide from resin and concomitant deprotection of the side chain protecting groupswas carried out by shaking in TFA/triisopropylsilane/H20 (95/2.5/2.5; 5 mL), at ambient temperature for3 h. Subsequent filtration aorded the peptide in the filtrate and the volume was reduced to 0.2 mL.Then, the crude peptides were precipitated by adding cold diethyl ether, and the crude peptides werethen purified by RP-HPLC. Synthesized peptides were characterized by NMR, and the high-resolutionmass spectroscopy.

Computed Properties

Molecular Weight:388.4
XLogP3:3.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:7
Exact Mass:388.14230712
Monoisotopic Mass:388.14230712
Topological Polar Surface Area:88.5
Heavy Atom Count:29
Complexity:555
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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