US 12,448,412 B2
Antigenic tripeptides derived from Mycobacterium avium subsp. paratuberculosis S-type strains, derivatives and uses thereof
John P. Bannantine, Ames, IA (US); Gilles Etienne, Toulouse (FR); Sylvie Bay, Paris (FR); and Franck Biet, Notre Dame D'Oe (FR)
Assigned to INSTITUT PASTEUR, Paris (FR); INSTITUT NATIONAL DE RECHERCHE POUR L'AGRICULTURE L'ALIMENTATION ET L'ENVIRONNEMENT, Paris (FR); and THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY OF AGRICULTURE, Washington, DC (US)
Filed by INSTITUT PASTEUR, Paris (FR); INSTITUT NATIONAL DE RECHERCHE POUR L'AGRICULTURE L'ALIMENTATION ET L'ENVIRONNEMENT, Paris (FR); and THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY OF AGRICULTURE, Washington, DC (US)
Filed on Mar. 15, 2024, as Appl. No. 18/606,817.
Application 18/606,817 is a division of application No. 17/938,865, filed on Oct. 7, 2022, granted, now 11,981,750.
Application 17/938,865 is a division of application No. 16/470,962, granted, now 11,498,942, issued on Nov. 15, 2022, previously published as PCT/EP2017/083924, filed on Dec. 20, 2017.
Claims priority of application No. PCT/IB2016/002018 (WO), filed on Dec. 20, 2016.
Prior Publication US 2024/0270790 A1, Aug. 15, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. C07K 5/087 (2006.01); A61K 39/04 (2006.01); A61K 47/54 (2017.01); A61K 47/60 (2017.01); C07K 7/06 (2006.01); C12Q 1/689 (2018.01); G01N 33/569 (2006.01)
CPC C07K 5/0812 (2013.01) [A61K 39/04 (2013.01); A61K 47/542 (2017.08); A61K 47/60 (2017.08); C07K 7/06 (2013.01); C12Q 1/689 (2013.01); G01N 33/5695 (2013.01); G01N 2333/5428 (2013.01); G01N 2333/57 (2013.01); G01N 2469/20 (2013.01); G01N 2800/26 (2013.01)] 14 Claims
 
1. A pentapeptide conjugate comprising a pentapeptide core having the sequence H-Phe-Val-Ile-Phe-Ala-OH (SEQ ID NO:13), wherein the 5 amino acids are independently natural amino acids or modified amino acids, and wherein the pentapeptide core is further modified by:
amidation of C-terminal Alanine with a polyethylene glycol moiety;
amidation of C-terminal Alanine with a polyethylene glycol moiety and N-acylation of the N-terminus;
modification of the N terminal Phenylalanine by addition of a polyethylene glycol moiety or
amidation of C-terminal Alanine with a first polyethylene glycol moiety and addition of a second polyethylene glycol moiety at the N-terminus of the pentapeptide, wherein said first and said second polyethylene glycol moieties are identical or different,
and wherein said pentapeptide conjugate is hydrosoluble.