Alternatived Products of [ 199807-35-7 ]
Product Details of [ 199807-35-7 ]
CAS No. : | 199807-35-7 |
MDL No. : | MFCD22665738 |
Formula : |
C29H41F3N8O9
|
Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | WHJCSACXAPYNTG-LOPTWHKWSA-N |
M.W : |
702.68
|
Pubchem ID : | 129626550 |
Synonyms : |
NSC 707544;EMD 121974;Cilengitide trifluoroacetate;EMD 121974 TFA
|
Safety of [ 199807-35-7 ]
Application In Synthesis of [ 199807-35-7 ]
* 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.
- Upstream synthesis route of [ 199807-35-7 ]
- Downstream synthetic route of [ 199807-35-7 ]
- 1
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C31H48N8O7
[ No CAS ]
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[ 76-05-1 ]
-
[ 199807-35-7 ]
Yield | Reaction Conditions | Operation in experiment |
|
In water; |
Fmoc-Arg(Mtr)-Gly-Asp(OBut)-DPhe-NMeVal-ONa (SEQ ID No. 14) is synthesized using solid-phase Merrifield-type procedures by sequentially adding NMeVal, DPhe, Asp(OBut), Gly and Fmoc-Arg(Mtr) in a step-wise manner to a 4-hydroxymethyl-phenoxymethyl-polystyrene resin (Wang type resin) (customary Merrifield-type methods of peptide synthesis are applied). The polystyrene resin and amino acid residues precursors are commercially available from Aldrich, Sigma or Fluka chemical companies). After completion of sequential addition of the amino acid residues, the resin is then eliminated from the peptide chain using a 1:1 mixture of TFA/dichloromethane which provides the Fmoc-Arg(Mtr)-Gly-Asp(OBut)-DPhe-NMeVal-OH product (SEQ ID No. 15). The Fmoc group is then removed with a 1:1 mixture of piperidine/DMF which provides the crude Arg(Mtr)-Gly-Asp(OBut)-DPhe-NMeVal-OH precursor (SEQ ID No. 16) which is then purified by HPLC in the customary manner.For cyclization, a solution of 0.6 g of Arg(Mtr)-Gly-Asp(OBut)-DPhe-NMeVal-OH (synthesized above) (SEQ ID No. 16) in 15 ml of DMF (dimethylformamide; Aldrich) is diluted with 85 ml of dichloromethane (Aldrich), and 50 mg of NaHCO3 are added. After cooling in a dry ice/acetone mixture, 40 mul of diphenylphosphoryl azide (Aldrich) are added. After standing at room temperature for 16 hours, the solution is concentrated. The concentrate is gel-filtered (Sephadex G10 column in isopropanol/water 8:2) and then purified by HPLC in the customary manner. Treatment with TFA (trifluoroacetic acid)/H2O (98:2) gives cyclo-(Arg-Gly-Asp-DPhe-NMeVal)(also referred to as ?cyclo(RGDfN-MeV)? herein; SEQ ID NO 11)×TFA which is then purified by HPLC in the customary manner; RT=19.5; FAB-MS (M+H): 589. |
- 2
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[ 199807-35-7 ]
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[ 188968-51-6 ]
Yield | Reaction Conditions | Operation in experiment |
|
In water;vacuum evaporation; |
TFA salt is removed from the above-produced cyclic peptide by suspending the cyclo-(Arg-Gly-Asp-DPhe-NMeVal) (SEQ ID NO 11).x.TFA in water followed by evaporation under vacuum to remove the TFA. The cyclic peptide formed is referred to as an "inner salt" and is designated cyclo-(Arg-Gly-Asp-DPhe-NMeVal) (SEQ ID NO 11). The term "inner salt" is used because the cyclic peptide contains two oppositely charged residues which intra-electronically counterbalance each other to form an overall noncharged molecule. One of the charged residues contains an acid moiety and the other charged residue contains an amino moiety. When the acid moiety and the amino moiety are in close proximity to one another, the acid moiety can be deprotonated by the amino moiety which forms a carboxylate/ammonium salt species with an overall neutral charge. |
|
With ammonium hydroxide; In water; at 20℃;pH 6.8; |
Example 19 Crystallization of the Inner Salt from the Trifluoroacetate (0900) 1.41 g cyclo-(Arg-Gly-Asp-DPhe-NMeVal)×TFA are dissolved in 10 ml water. By use of conc. aqueous ammonia pH is adjusted to ?6.8. After standing over night at ambient temperature, crystals appear, which are separated by filtration, washed with ice-cold water, and dried on air. Mother liquor is concentrated to yield addition crystalline product. |