Synthesis of Alicyclic<i>trans-</i>β-Amino Acids from<i>cis</i>-β-Hydroxycycloalkane­carboxylates

Kiss, Lóránd; Forró, Enikő; Bernáth, G.; Fülöp, Ferenc

doi:10.1055/s-2005-861875

Synthesis

2005

DOI: 10.1055/s-2005-861875

|View full text |Cite

Synthesis of Alicyclictrans-β-Amino Acids fromcis-β-Hydroxycycloalkanecarboxylates

Lóránd Kiss

Enikő Forró

G. Bernáth

et al.

Abstract: A simple and efficient method is described for the preparation of both racemic and enantiopure trans-b-amino acids with a cycloheptane or cyclooctane skeleton, starting from racemic and enantiopure ethyl cis-2-hydroxycarboxylates.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2023

Publication Types

Select...

Article1

Relationship

Self Cite0

Independent1

Authors

Journals

Cited by 1 publication

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Exploring a β-Amino Acid with a Seven-Membered Ring Constraint as a Foldamer Building Block for Nontraditional Helices

Seo,

Son,

Kim

et al. 2023

Org. Lett.

View full text Add to dashboard Cite

We explored trans-and cis-2-aminocycloheptanecarboxylic acid (ACHpC) as potential building blocks for helical foldamers. trans-ACHpC does not show sufficient folding propensity in unnatural peptides. cis-ACHpC promotes nontraditional helices of two unnatural peptide backbones: the 11/9-helix for 1:1 α/β-peptides and the 12/10-helix for β-peptides with interconvertible handedness. The two opposite-handed 12/10helices rapidly interconvert in solution by pseudorotation of the two twist chair forms of the cycloheptane moiety in each cis-ACHpC residue.

show abstract

Exploring a β-Amino Acid with a Seven-Membered Ring Constraint as a Foldamer Building Block for Nontraditional Helices

Seo,

Son,

Kim

et al. 2023

Org. Lett.

View full text Add to dashboard Cite

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Synthesis of Alicyclictrans-β-Amino Acids fromcis-β-Hydroxycycloalkanecarboxylates

Abstract: A simple and efficient method is described for the preparation of both racemic and enantiopure trans-b-amino acids with a cycloheptane or cyclooctane skeleton, starting from racemic and enantiopure ethyl cis-2-hydroxycarboxylates.

Cited by 1 publication

References 11 publications

Exploring a β-Amino Acid with a Seven-Membered Ring Constraint as a Foldamer Building Block for Nontraditional Helices

Exploring a β-Amino Acid with a Seven-Membered Ring Constraint as a Foldamer Building Block for Nontraditional Helices

Contact Info

Product

Resources

About

Synthesis of Alicyclictrans-β-Amino Acids fromcis-β-Hydroxycycloalkane­carboxylates

Abstract: A simple and efficient method is described for the preparation of both racemic and enantiopure trans-b-amino acids with a cycloheptane or cyclooctane skeleton, starting from racemic and enantiopure ethyl cis-2-hydroxycarboxylates.

Cited by 1 publication

References 11 publications

Exploring a β-Amino Acid with a Seven-Membered Ring Constraint as a Foldamer Building Block for Nontraditional Helices

Exploring a β-Amino Acid with a Seven-Membered Ring Constraint as a Foldamer Building Block for Nontraditional Helices

Contact Info

Product

Resources

About

Synthesis of Alicyclictrans-β-Amino Acids fromcis-β-Hydroxycycloalkanecarboxylates