title: Bulky melamine-based Zn-porphyrin tweezer as a CD probe of molecular chirality.
abstract: The transfer of chirality from a guest molecule to an achiral host is the subject of significant interest especially when, upon chiral induction, the chiroptical response of the host/guest complex can effectively report the absolute configuration (AC) of the guest. For more than a decade, dimeric metalloporphyrin hosts (tweezers) have been successfully applied as chirality probes for determination of the AC for a wide variety of chiral synthetic compounds and natural products. The objective of this study is to investigate the utility of a new class of melamine-bridged Zn-porphyrin tweezers as sensitive AC reporters. A combined approach based on an experimental CD analysis and a theoretical prediction of the prevailing interporphyrin helicity demonstrates that these tweezers display favorable properties for chiral recognition. Herein, we discuss the application of the melamine-bridged tweezer to the chiral recognition of a diverse set of chiral guests, such as 1,2-diamines, α-amino-esters and amides, secondary alcohols, and 1,2-amino-alcohols. The bulky periphery and the presence of a rigid porphyrin linkage lead, in some cases, to a more enhanced CD sensitivity than that reported earlier with other tweezers.
authors.affiliation: Department of Life Sciences, New York Institute of Technology (NYIT), New York, New York, USA.
authors.forename: Ana G
authors.initials: AG
authors.lastname: Petrovic
authors.forename: Ghislaine
authors.initials: G
authors.lastname: Vantomme
authors.forename: Yashira L
authors.initials: YL
authors.lastname: Negrón-Abril
authors.forename: Elisa
authors.initials: E
authors.lastname: Lubian
authors.forename: Giacomo
authors.initials: G
authors.lastname: Saielli
authors.forename: Ileana
authors.initials: I
authors.lastname: Menegazzo
authors.forename: Roselynn
authors.initials: R
authors.lastname: Cordero
authors.forename: Gloria
authors.initials: G
authors.lastname: Proni
authors.forename: Koji
authors.initials: K
authors.lastname: Nakanishi
authors.forename: Tommaso
authors.initials: T
authors.lastname: Carofiglio
authors.forename: Nina
authors.initials: N
authors.lastname: Berova
mesh_terms: D000438:Alcohols / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D000605:Amino Alcohols / Q000737:chemistry; D002942:Circular Dichroism / Q000379:methods*; D003198:Computer Simulation; D003959:Diamines / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008665:Metalloporphyrins / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D013056:Spectrophotometry, Ultraviolet / Q000379:methods; D014227:Triazines / Q000737:chemistry*
chemical_list: D000438:Alcohols; D000588:Amines; D000605:Amino Alcohols; D003959:Diamines; D008665:Metalloporphyrins; D014227:Triazines; C017802:zinc hematoporphyrin; C011907:melamine