A facile approach towards amidinophenylalanine derivatives as building blocks for the synthesis of non-natural peptides and peptidomimetics

The amidine function is extensively utilized as synthetic intermediate for structurally diverse heterocycles and as a core element in drugs and drug candidates. This study describes a facile and convenient approach for the highly efficient synthesis of amidinophenylalanine derivatives via the reduct...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Hauptverfasser: Behrouz, Somayeh (VerfasserIn) , Kühl, Nikos (VerfasserIn) , Klein, Christian D. (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 22 August 2021
In: Tetrahedron letters
Year: 2021, Jahrgang: 81, Pages: 1-7
ISSN:1873-3581
DOI:10.1016/j.tetlet.2021.153342
Online-Zugang:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1016/j.tetlet.2021.153342
Verlag, lizenzpflichtig, Volltext: https://www.sciencedirect.com/science/article/pii/S0040403921006006
Volltext
Verfasserangaben:Somayeh Behrouz, Nikos Kühl, Christian D. Klein

MARC

LEADER 00000caa a2200000 c 4500
001 1779374739
003 DE-627
005 20230426132944.0
007 cr uuu---uuuuu
008 211126s2021 xx |||||o 00| ||eng c
024 7 |a 10.1016/j.tetlet.2021.153342  |2 doi 
035 |a (DE-627)1779374739 
035 |a (DE-599)KXP1779374739 
035 |a (OCoLC)1341434433 
040 |a DE-627  |b ger  |c DE-627  |e rda 
041 |a eng 
084 |a 30  |2 sdnb 
100 1 |a Behrouz, Somayeh  |e VerfasserIn  |0 (DE-588)1246535939  |0 (DE-627)1779374046  |4 aut 
245 1 2 |a A facile approach towards amidinophenylalanine derivatives as building blocks for the synthesis of non-natural peptides and peptidomimetics  |c Somayeh Behrouz, Nikos Kühl, Christian D. Klein 
264 1 |c 22 August 2021 
300 |a 7 
336 |a Text  |b txt  |2 rdacontent 
337 |a Computermedien  |b c  |2 rdamedia 
338 |a Online-Ressource  |b cr  |2 rdacarrier 
500 |a Gesehen am 26.11.2021 
520 |a The amidine function is extensively utilized as synthetic intermediate for structurally diverse heterocycles and as a core element in drugs and drug candidates. This study describes a facile and convenient approach for the highly efficient synthesis of amidinophenylalanine derivatives via the reduction of amidoximophenylalanines in the presence of Ac2O/AcOH/Zn at room temperature. The described process is attractive for process and medicinal chemistry due to its facility, safety, low cost, applicability for hydrogenation-sensitive compounds, and efficiency. Using this method, amidinophenylalanine derivatives as building blocks for peptides were obtained in excellent yields. 
650 4 |a Amidines 
650 4 |a Amidoximes 
650 4 |a Phenylalanine derivatives 
650 4 |a Reduction 
650 4 |a Zinc 
700 1 |a Kühl, Nikos  |d 1991-  |e VerfasserIn  |0 (DE-588)1218234296  |0 (DE-627)1733653430  |4 aut 
700 1 |a Klein, Christian D.  |e VerfasserIn  |0 (DE-588)1060644894  |0 (DE-627)800410157  |0 (DE-576)416768717  |4 aut 
773 0 8 |i Enthalten in  |t Tetrahedron letters  |d Amsterdam [u.a.] : Elsevier Science, 1959  |g 81(2021), Artikel-ID 153342, Seite 1-7  |h Online-Ressource  |w (DE-627)320459489  |w (DE-600)2007074-3  |w (DE-576)094107939  |x 1873-3581  |7 nnas  |a A facile approach towards amidinophenylalanine derivatives as building blocks for the synthesis of non-natural peptides and peptidomimetics 
773 1 8 |g volume:81  |g year:2021  |g elocationid:153342  |g pages:1-7  |g extent:7  |a A facile approach towards amidinophenylalanine derivatives as building blocks for the synthesis of non-natural peptides and peptidomimetics 
856 4 0 |u https://doi.org/10.1016/j.tetlet.2021.153342  |x Verlag  |x Resolving-System  |z lizenzpflichtig  |3 Volltext 
856 4 0 |u https://www.sciencedirect.com/science/article/pii/S0040403921006006  |x Verlag  |z lizenzpflichtig  |3 Volltext 
951 |a AR 
992 |a 20211126 
993 |a Article 
994 |a 2021 
998 |g 1060644894  |a Klein, Christian D.  |m 1060644894:Klein, Christian D.  |d 160000  |d 160100  |e 160000PK1060644894  |e 160100PK1060644894  |k 0/160000/  |k 1/160000/160100/  |p 3  |y j 
998 |g 1218234296  |a Kühl, Nikos  |m 1218234296:Kühl, Nikos  |d 160000  |d 160100  |e 160000PK1218234296  |e 160100PK1218234296  |k 0/160000/  |k 1/160000/160100/  |p 2 
998 |g 1246535939  |a Behrouz, Somayeh  |m 1246535939:Behrouz, Somayeh  |p 1  |x j 
999 |a KXP-PPN1779374739  |e 4007997586 
BIB |a Y 
SER |a journal 
JSO |a {"note":["Gesehen am 26.11.2021"],"language":["eng"],"relHost":[{"recId":"320459489","physDesc":[{"extent":"Online-Ressource"}],"note":["Gesehen am 15.11.2023"],"type":{"bibl":"periodical","media":"Online-Ressource"},"pubHistory":["1.1959/60 -"],"language":["eng"],"id":{"issn":["1873-3581"],"eki":["320459489"],"zdb":["2007074-3"]},"part":{"pages":"1-7","volume":"81","extent":"7","text":"81(2021), Artikel-ID 153342, Seite 1-7","year":"2021"},"origin":[{"publisherPlace":"Amsterdam [u.a.]","dateIssuedKey":"1959","publisher":"Elsevier Science","dateIssuedDisp":"1959-"}],"disp":"A facile approach towards amidinophenylalanine derivatives as building blocks for the synthesis of non-natural peptides and peptidomimeticsTetrahedron letters","title":[{"title":"Tetrahedron letters","title_sort":"Tetrahedron letters"}]}],"recId":"1779374739","physDesc":[{"extent":"7 S."}],"type":{"media":"Online-Ressource","bibl":"article-journal"},"name":{"displayForm":["Somayeh Behrouz, Nikos Kühl, Christian D. Klein"]},"title":[{"title_sort":"facile approach towards amidinophenylalanine derivatives as building blocks for the synthesis of non-natural peptides and peptidomimetics","title":"A facile approach towards amidinophenylalanine derivatives as building blocks for the synthesis of non-natural peptides and peptidomimetics"}],"origin":[{"dateIssuedKey":"2021","dateIssuedDisp":"22 August 2021"}],"person":[{"given":"Somayeh","family":"Behrouz","role":"aut","display":"Behrouz, Somayeh"},{"display":"Kühl, Nikos","role":"aut","family":"Kühl","given":"Nikos"},{"given":"Christian D.","display":"Klein, Christian D.","role":"aut","family":"Klein"}],"id":{"doi":["10.1016/j.tetlet.2021.153342"],"eki":["1779374739"]}} 
SRT |a BEHROUZSOMFACILEAPPR2220