US 11,834,468 B2
Protected tetrasaccharides, their process of preparation and their use as transglucosylase acceptor substrates in the chemo-enzymatic synthesis of Shigella flexneri specific oligosaccharides
Laurence Mulard, Le Kremlin Bicetre (FR); Guillaume Le Heiget, Paris (FR); Zhaohu Hu, Wuhan (CN); Louis-Antoine Barel, Royat (FR); Isabelle Andre, Toulouse (FR); Claire Moulis, Vieillevigne (FR); Magali Remaud-Simeon, Ramonville (FR); Sophie Barbe, Goyrans (FR); Mounir Benkoulouche, Villenave d'Ornon (FR); and Akli Ben Imeddourene, Toulouse (FR)
Assigned to INSTITUT PASTEUR, Paris (FR); INSTITUT NATIONAL DE LA RECHERCHE AGRONOMIQUE, Paris (FR); INSTITUT NATIONAL DES SCIENCES APPLIQUEES DE TOULOUSE, Toulouse (FR); and CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, Paris (FR)
Appl. No. 16/627,729
Filed by INSTITUT PASTEUR, Paris (FR); INSTITUT NATIONAL DE LA RECHERCHE AGRONOMIQUE, Paris (FR); INSTITUT NATIONAL DES SCIENCES APPLIQUEES DE TOULOUSE, Toulouse (FR); and CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, Paris (FR)
PCT Filed Jul. 3, 2018, PCT No. PCT/EP2018/068013
§ 371(c)(1), (2) Date Dec. 30, 2019,
PCT Pub. No. WO2019/007999, PCT Pub. Date Jan. 10, 2019.
Claims priority of provisional application 62/528,277, filed on Jul. 3, 2017.
Prior Publication US 2020/0165285 A1, May 28, 2020
Int. Cl. C07H 15/10 (2006.01); C07H 15/203 (2006.01); C07H 13/04 (2006.01); C12P 19/04 (2006.01); C12P 19/14 (2006.01); C12P 19/18 (2006.01); C12P 19/28 (2006.01)
CPC C07H 15/10 (2013.01) [C07H 13/04 (2013.01); C07H 15/203 (2013.01); C12P 19/04 (2013.01); C12P 19/14 (2013.01); C12P 19/18 (2013.01); C12P 19/28 (2013.01)] 19 Claims
 
1. A compound of following formula (I0):
(TD)xABzC(TD)y-R  (I0)
wherein:
x and y are 0 or 1, providing x+y=1;
A is 2)-α-L-Rhap-(1→;
B is 2)-α-L-Rhap-(1→;
C is 3)-α-L-Rhap-(1→;
D is 3)-α-D-GlcpN-(1→ or 3)-β-D-GlcpN-14;
Z represents ClAc or BrAc;
T is chosen from trichloroacetyl (Cl3Ac), 2,2,2-trichloroethoxycarbonyl (Troc) or allyloxycarbonyl (Alloc), or is azide (N3);
R is chosen from allyl (All), para-methoxyphenyl (PMP), pentenyl (Pent), phenyl (Ph), triisopropylsilyl (TIPS) or tert-butyldiphenylsilyl (TBDPS) group;
ClAc is ClCH2—C(O)—; and
BrAc is BrCH2—C(O)—
and all other hydroxyl groups of A, B, C, and D are unprotected —OH groups.