Stereodivergent Chirality Transfer by Noncovalent Control of Disulfide Bonds.
J Am Chem Soc
; 144(10): 4376-4382, 2022 03 16.
Article
em En
| MEDLINE
| ID: mdl-35120292
ABSTRACT
Controlling dynamic stereochemistry is an important challenge, as it is not only inherent to protein structure and function but often governs supramolecular systems and self-assembly. Typically, disulfide bonds exhibit stereodivergent behavior in proteins; however, how chiral information is transmitted to disulfide bonds remains unclear. Here, we report that hydrogen bonds are essential in the control of disulfide chirality and enable stereodivergent chirality transfer. The formation of S-S···H-N hydrogen bonds in solution can drive conformational adaption to allow intramolecular chirality transfer, while the formation of C=O···H-N hydrogen bonds results in supramolecular chirality transfer to form antiparallel helically self-assembled solid-state architectures. The dependence on the structural information encoded in the homochiral amino acid building blocks reveals the remarkable dynamic stereochemical space accessible through noncovalent chirality transmission.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Dissulfetos
/
Hidrogênio
Idioma:
En
Ano de publicação:
2022
Tipo de documento:
Article