Structure of H-D-Phe-D-Phe-OH
CAS No.: 58607-69-5
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CAS No. : | 58607-69-5 |
Formula : | C18H20N2O3 |
M.W : | 312.36 |
SMILES Code : | O=C(O)[C@H](NC([C@H](N)CC1=CC=CC=C1)=O)CC2=CC=CC=C2 |
MDL No. : | MFCD00237217 |
InChI Key : | GKZIWHRNKRBEOH-HZPDHXFCSA-N |
Pubchem ID : | 6426953 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Loading of the 2-Chlorotrityl Chloride Resin (GP 1): The amino acid (3 equiv. rel. to the resin)and 6 equiv. of DIPEA were dissolved in CH2Cl2 (10 mL per 1 g of the resin), containing, if necessary,a small amount of DMF to facilitate dissolution of the amino acid. The 2-chlorotrityl chloride resinwas pre-swollen in CH2Cl2 for 1 h, and, after that the solution containing the amino acid was added.The resin was shaken for 30-120 min, then washed three times with CH2Cl2/MeOH/DIPEA (17:2:1),twice with DMF and three times with CH2Cl2.Standard Coupling Procedure (GP 2): Three equiv. of amino acid, 3 equiv. of 4-(4,6dimethoxy-[1,3,5]triazin-2-yl)-4-methylmorpholinium toluene-4-sulfonate (DMT/NMM/TosO-) and6 equiv. of NMM were mixed and added to the resin. The resin was shaken for 1-2 h. The Kaiser testwas used to confirm completion of the reaction [58].Deprotection (GP 3): The Fmoc protecting group was removed using a solution of 20% piperidinein DMF (2 x 5 min).Cleavage from the Resin (GP 4): The peptides were cleaved from the resin using TFA/Et3SiH/H2O95:2.5:2.5 (ca. 2 mL/0.1 g of resin). Cleavage was performed over 4 h. The resin was filtered off andthe filtrate evaporated. To precipitate the peptide, Et2O was added to the oily residue. The resultingsolid was filtered off, washed with Et2O, dried and lyophilized.Cleavage from the Resin (GP 4A): The peptides were cleaved from the resin usingTFA/EDT/Et3SiH/H2O 94:2.5:2.5:1 (ca. 2 mL/0.1 g of resin). Cleavage was performed over 4 h.The resin was filtered off and the filtrate evaporated. To precipitate the peptide, Et2O was added to theoily residue. The resulting solid was filtered off, washed with Et2O, dried and lyophilized. |