Practical Synthesis of Phosphinic Dipeptides by Tandem Esterification of Aminophosphinic and Acrylic Acids under Silylating Conditions

Επιστημονική δημοσίευση - Άρθρο Περιοδικού uoadl:3020017 34 Αναγνώσεις

Μονάδα:
Ερευνητικό υλικό ΕΚΠΑ
Τίτλος:
Practical Synthesis of Phosphinic Dipeptides by Tandem Esterification of Aminophosphinic and Acrylic Acids under Silylating Conditions
Γλώσσες Τεκμηρίου:
Αγγλικά
Περίληψη:
In this report, a synthetic protocol for the preparation of phosphinic dipeptides of type 5 is presented. These compounds serve as valuable building blocks for the development of highly potent phosphinopeptidic inhibitors of medicinally relevant Zn-metalloproteases and aspartyl proteases. The proposed method is based on the tandem esterification of α-aminophosphinic and acrylic acids under silylating conditions in order to subsequently participate in a P-Michael reaction. The scope of the transformation was investigated by using a diverse set of readily available acrylic acids and (R)-α-aminophosphinic acids, and high yields were achieved in all cases. In most examples reported herein, the isolation of biologically relevant (R,S)-diastereoisomers became possible by simple crystallization from the crude products, thus enhancing the operational simplicity of the proposed method. Finally, functional groups corresponding to acidic or basic natural amino acids are also compatible with the reaction conditions. Based on the above, we expect that the practicality of the proposed protocol will facilitate the discovery of pharmacologically useful bioactive phosphinic peptides. © 2022 by the authors. Licensee MDPI, Basel, Switzerland.
Έτος δημοσίευσης:
2022
Συγγραφείς:
Kokkala, P.
Voreakos, K.
Lelis, A.
Patiniotis, K.
Skoulikas, N.
Devel, L.
Ziotopoulou, A.
Kaloumenou, E.
Georgiadis, D.
Περιοδικό:
Molecules
Εκδότης:
MDPI
Τόμος:
27
Αριθμός / τεύχος:
4
Λέξεις-κλειδιά:
acrylic acid; acrylic acid derivative; dipeptide; phosphinic acid derivative, chemistry; esterification; synthesis, Acrylates; Dipeptides; Esterification; Phosphinic Acids
Επίσημο URL (Εκδότης):
DOI:
10.3390/molecules27041242
Το ψηφιακό υλικό του τεκμηρίου δεν είναι διαθέσιμο.