Unexpected Internal Peptide Butoxycarbonylation of a Linear N‐Me Amide Peptide Derived from Virginiamycin S and Resulting Failure for a Carboxy‐Terminal Sequencing. Preparation of the Tetrapeptide Synthon Thr‐D‐Abu‐Pro‐MePhe‐OBzl

We achieved the reconstruction of VS1‐analogues containing a substitute for the fifth residue, γ‐oxo‐Pip (Pip = pipecolic acid), starting from VS1‐pentapeptide (VS5P; 3) the latter being prepared by a two‐step degradation process of the native antibiotic VS1 (1a). Protecting groups during the procedure were chosen in order to realize a minimal number of steps. Most of these gave excellent yields, including final cyclization between the fourth and fifth residue. In total, four analogues were synthesized with Ala, Asp, Asn and Lys (1b) replacing γ‐oxo‐Pip. Among these, [Lys5(Tfa salt)]‐VS1 is water‐soluble, which is an important characteristic for eventual application of VS1 as a pharmaceutical agent. In the proposed reaction sequence, we made sure that residues 4 (MePhe) and 6 (Phg) became partially epimerised. We therefore obtained each time after cyclization a total of four epimers that have been separated by preparative TLC. The chiral identity of the final residues was realized by GC (Chirasil Val®‐III) on the total hydrolysates.

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.

Unexpected Internal Peptide Butoxycarbonylation of a Linear N‐Me Amide Peptide Derived from Virginiamycin S and Resulting Failure for a Carboxy‐Terminal Sequencing. Preparation of the Tetrapeptide Synthon Thr‐D‐Abu‐Pro‐MePhe‐OBzl

Cited by 2 publications

References 21 publications

Preparation of des-3-hydroxy-picolinoyl pristinamycins I

Preparation of des-3-hydroxy-picolinoyl pristinamycins I

Partial synthesis of five new analogues of the peptido‐lactone Virginiamycine S₁, modified in the fifth and/or sixth position ([Xxx⁵]‐VS₁ with Xxx = Ala, Asp, Asn and Lys and [Ala⁵,Gly⁶]‐VS₁)

Contact Info

Product

Resources

About

Unexpected Internal Peptide Butoxycarbonylation of a Linear N‐Me Amide Peptide Derived from Virginiamycin S and Resulting Failure for a Carboxy‐Terminal Sequencing. Preparation of the Tetrapeptide Synthon Thr‐D‐Abu‐Pro‐MePhe‐OBzl

Cited by 2 publications

References 21 publications

Preparation of des-3-hydroxy-picolinoyl pristinamycins I

Preparation of des-3-hydroxy-picolinoyl pristinamycins I

Partial synthesis of five new analogues of the peptido‐lactone Virginiamycine S1, modified in the fifth and/or sixth position ([Xxx5]‐VS1 with Xxx = Ala, Asp, Asn and Lys and [Ala5,Gly6]‐VS1)

Contact Info

Product

Resources

About

Partial synthesis of five new analogues of the peptido‐lactone Virginiamycine S₁, modified in the fifth and/or sixth position ([Xxx⁵]‐VS₁ with Xxx = Ala, Asp, Asn and Lys and [Ala⁵,Gly⁶]‐VS₁)