Some Simple Conjugates of Virginiamycin and their Bioactivity

AbseactThe picolinic hydroxyl in Virginiamycin S (VS ; &a) can be protected with di-tart-butyloxycarbonate affording the tertlbutyloxycarbonyl derivative thus yielding VS -1'-0-Boc (u) in a fast and quantitative conversion without concomitant be4aSne (&) formation. Once protected however, the lactone bond in J& can no longer be cleaved under mild alkaline conditions. A possible explanation is given. INTRQDU(ITI0M

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Unique 1′‐O‐boc protection of Virginiamycin S and Resulting Resistance Against Sodium Hydroxide

Moerman

Anteunis

1991

Bulletin des Soc Chimique

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A progressive synthetic strategy for class B synergimycins

Robinson

Taylor

Liotta

et al. 2004

Tetrahedron Letters

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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)

Moerman

Anteunis

1993

International Journal of Peptide and Protein Research

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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.

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Some Simple Conjugates of Virginiamycin and their Bioactivity

Abstract: Derivatives of the native antibioticum Viginiamycin S1 (1) conjugated at the pipecolic acid 0x0 position (5-J.2) have been prepared and their bioactivity tested together with some earlier prepared congeners (I, u-s).

Cited by 5 publications

References 10 publications

Unique 1′‐O‐boc protection of Virginiamycin S and Resulting Resistance Against Sodium Hydroxide

Unique 1′‐O‐boc protection of Virginiamycin S and Resulting Resistance Against Sodium Hydroxide

A progressive synthetic strategy for class B synergimycins

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)

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Some Simple Conjugates of Virginiamycin and their Bioactivity

Abstract: Derivatives of the native antibioticum Viginiamycin S1 (1) conjugated at the pipecolic acid 0x0 position (5-J.2) have been prepared and their bioactivity tested together with some earlier prepared congeners (I, u-s).

Cited by 5 publications

References 10 publications

Unique 1′‐O‐boc protection of Virginiamycin S and Resulting Resistance Against Sodium Hydroxide

Unique 1′‐O‐boc protection of Virginiamycin S and Resulting Resistance Against Sodium Hydroxide

A progressive synthetic strategy for class B synergimycins

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)

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Product

Resources

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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)