| Revision as of 21:31, 7 August 2011 editRjwilmsi (talk | contribs)Extended confirmed users, Pending changes reviewers, Rollbackers932,125 editsm Journal cites:, added 1 PMID, using AWB (7794)← Previous edit |
Latest revision as of 16:33, 17 September 2023 edit undoKoIobok (talk | contribs)Extended confirmed users1,350 edits Changed Category:Amino acids to Category:Alpha-Amino acids |
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{{orphan|date=January 2009}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 399909386 |
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| verifiedrevid = 443570999 |
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| Name = Diphenylalanine |
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| Name = Diphenylalanine |
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| ImageFile = Diphenylalanine structure.svg |
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| ImageFile = Diphenylalanine structure.svg |
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| ImageSize = 150px |
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| ImageSize = 150px |
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| ImageName = Diphenylalanine |
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| ImageName = Diphenylalanine |
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| IUPACName = 2-amino-3,3-diphenyl-propionic acid |
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| PIN = 2-Amino-3,3-diphenylpropanoic acid |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| index1_label = ({{small|L}}-isomer) |
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| index2_label = ({{small|D}}-isomer) |
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| SMILES = OC(C(N)C(C2=CC=CC=C2)C1=CC=CC=C1)=O |
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| SMILES = OC(C(N)C(C2=CC=CC=C2)C1=CC=CC=C1)=O |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID1 = 143073 |
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| ChemSpiderID = 10608219 |
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| InChI = 1/C15H15NO2/c1-12(15(17)18)16(13-8-4-2-5-9-13)14-10-6-3-7-11-14/h2-12H,1H3,(H,17,18) |
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| InChIKey = SAUDSWFPPKSVMK-UHFFFAOYAY |
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| SMILES1 = CC(N(c1ccccc1)c2ccccc2)C(O)=O |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C15H15NO2/c1-12(15(17)18)16(13-8-4-2-5-9-13)14-10-6-3-7-11-14/h2-12H,1H3,(H,17,18) |
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| StdInChI = 1S/C15H15NO2/c1-12(15(17)18)16(13-8-4-2-5-9-13)14-10-6-3-7-11-14/h2-12H,1H3,(H,17,18) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = SAUDSWFPPKSVMK-UHFFFAOYSA-N |
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| StdInChIKey = SAUDSWFPPKSVMK-UHFFFAOYSA-N |
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| CASNo1_Ref = {{cascite|correct|??}} |
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| CASNo = 149597-92-2 |
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| CASOther = (L-isomer)<br>149597-91-1 (D-isomer) |
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| CASNo1 = 149597-92-2 |
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| CASNo_Comment = |
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| CASNo2_Ref = {{cascite|correct|??}} |
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⚫ |
| CASNo2 = 149597-91-1 |
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| PubChem1 = 162977 |
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| PubChem2 = 1520861 |
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| UNII1 = L1ZWG54X8B |
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| UNII2 = H2JAP020MP |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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}} |
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| Section8 = {{Chembox Related |
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| Section8 = {{Chembox Related |
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| Function = ]s |
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| OtherFunction_label = ]s |
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| OtherFunctn = ] |
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| OtherFunction = ] |
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'''Diphenylalanine''' is an unnatural ]. It is similar to the two ]s ] and ]. It has been used for the synthesis of ] analogues which are capable to inhibit certain ].<ref>{{cite journal |
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'''Diphenylalanine''' is a term that has recently been used to describe the unnatural ] similar to the two ]s ] and ]. It has been used for the synthesis of ] analogues which are capable of inhibiting certain ].<ref>{{cite journal |
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| title = Synthesis and biological activity of ketomethylene pseudopeptide analogs as thrombin inhibitors |
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| title = Synthesis and biological activity of ketomethylene pseudopeptide analogs as thrombin inhibitors |
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| author = Leifeng Cheng, Christopher A. Goodwin, Michael F. Schully, Vijay V. Kakkar, and Goran Claeson |
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|author1=Leifeng Cheng |author2=Christopher A. Goodwin |author3=Michael F. Schully |author4=Vijay V. Kakkar |author5=Goran Claeson | journal = ] |
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| journal = ] |
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| year = 1992 |
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| year = 1992 |
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| volume = 35 |
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| volume = 35 |
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}}</ref> |
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}}</ref> |
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Individual ]s of this compound can be synthesized via ] of a ] ] derivative of 3,3-diphenylpropanoic acid.<ref>{{cite journal |
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A possible synthesis starts from 3,3-diphenyl-] which is stereoselective aminated to the diphenylalanine.<ref>{{cite journal |
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| title = Chiral cynthesis of D- and L-3,3-diphenylalanine (DIP), unusual α-amino acids for peptides of biological interest |
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| title = Chiral cynthesis of <small>D</small>- and <small>L</small>-3,3-diphenylalanine (Dip), unusual α-amino acids for peptides of biological interest |
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| author = Huai G. Chen, V. G. Beylin, M. Marlatt, B. Leja and O. P. Goel, |
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| author1 = Huai G. Chen |author2= V. G. Beylin |author3= M. Marlatt |author4= B. Leja |author5= O. P. Goel |
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| journal = ] |
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| journal = ] |
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| year = 1992 |
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| year = 1992 |
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| doi = 10.1016/S0040-4039(00)92070-7 |
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| doi = 10.1016/S0040-4039(00)92070-7 |
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}}</ref> |
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}}</ref> |
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A historical use of the term ''diphenylalanine'' refers to the ] of phenylalanine ({{ill|Phe-Phe|WD=Q27140102}}). |
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==References== |
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==References== |
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{{reflist}} |
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{{reflist}} |
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