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Chemical Structure| 331432-79-2 Chemical Structure| 331432-79-2

Structure of 331432-79-2

Chemical Structure| 331432-79-2

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Product Citations

Marija Matkovi´c ;

Abstract: Diarylethene (DAE) molecular photoswitches draw attention as building units in the preparation of diverse photoactive molecules. An interesting class of these molecules are photoactive peptides. A way to build DAE moiety into peptides/peptidomimetics is via DAE amino acids, an example of which has been demonstrated in bioactive cyclic peptides, wherein the DAE Fmoc-amino acid was prepared and used. Herein, the preparation of DAE Boc-amino acid is presented using a modified method of synthesis. This contribution to the DAE amino acid collection could be useful in the further enhancement of diversity in designing different routes to photoactive peptides.

Keywords: molecular photoswitches ; diarylethene amino acids ; photoactive peptides

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Product Details of [ 331432-79-2 ]

CAS No. :331432-79-2
Formula : C17H16O4S2
M.W : 348.44
SMILES Code : O=C(C1=CC(C2=C(C3=C(C)SC(C(O)=O)=C3)CCC2)=C(C)S1)O
MDL No. :MFCD19382350

Safety of [ 331432-79-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Application In Synthesis of [ 331432-79-2 ]

* 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 [ 331432-79-2 ]

[ 331432-79-2 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 35661-51-9 ]
  • [ 331432-79-2 ]
  • C32H28N2O5S2 [ No CAS ]
  • C47H40N4O6S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide; In N,N-dimethyl-formamide; The starting dicarboxylic acid 2 used for the synthesis of lb was obtained as described in the literature [S. Gronowitz, K. Stenhamar, L. Svensson, Heterocycles 1981, 15, 947; T. B. Norsten, N. R. Branda, J Am. Chem. Soc.2001, 123, 1784].10105] Compound 2 (5 g, 14.3 mmol) was dissolved in dimethylformamide (25 ml). N,N-diisopropylcarbodiimide (DIC, 1.76 g, 14 mmol) and subsequently N,N-diisopropylethylamine (DIPEA, 3.7 g, 28.6 mmol) were added to the solution. Fmoc-hydrazine (Fmoc-NH--NH2 3.56 g; 14 mmol) was added immediately. Afier stirring the reaction mixture overnight it was poured into water (100 ml). The precipitate was filtered, dissolved in dichloromethane (200 ml) and washed twice with 0.5 M aq solution of sodium bicarbonate (100 ml), then with 0.5 M aq solution of hydrochloric acid (100 ml) in order to remove the unreacted dicarboxylic acid.10106] The organic phase was dried with magnesium sulfate. Evaporation of dichloromethane under reduced pressure gave the crude material which contained, along with the desirable 1 b, also the by-product 3. The by-product did not interfere with the solid-phase peptide synthesis, so the obtained material was used without additional purification. The analytically pure 1 b can be obtained using RP-HPLC (acetonitrile/water mixture as the eluent).10107] ?H-NMR (500 MHz, DMSO-d 6), 5=1.90 (s, 3H, CH3), 1.94 (s, 3H, CH3), 1.95-2.05 (m, 2H), 2.79 (t, J=7.8 Hz, 4H), 4.2-4.4 (system CH2CH, two rotamers 4:1), 7.17-7.91 (m, aromatic protons, 101), 9.00-9.36 (rotamers1:4, 11), 10.22-10.46 (rotamers 4:1, 11).
 

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