반응 #2143499

ord-086e8bb1cf0a459f9556f5cb8f0fee95

반응 방정식

O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1
UTP
C=C(OP(=O)(O)O)C(=O)O
PEP
O=P(O)(O)OC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
Glc-1-P
C=C(OP(=O)(O)O)C(=O)O
phosphoenolpyruvate
O=P(O)(O)OC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
Glc-1-P
O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1
UDP
Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O
ATP
CC(=O)C(=O)[O-]
pyruvate
O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1
UTP
O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1
UDP
→
O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H]2O)c(=O)[nH]1
UDP-Glc

반응물

O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1
UTP
—
1-13C Gal
C=C(OP(=O)(O)O)C(=O)O
PEP
O=P(O)(O)OC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
Glc-1-P
C=C(OP(=O)(O)O)C(=O)O
phosphoenolpyruvate
O=P(O)(O)OC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
Glc-1-P
O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1
UDP
Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O
ATP
CC(=O)C(=O)[O-]
pyruvate
—
Compound 40
O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1
UTP
O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1
UDP

시약

없음

반응 조건

상세 조건
See reaction.notes.procedure_details.

실험 절차

The multi-enzyme system (Scheme 15) started with 1-13C-Gal, [99 Atom Percent, purchased from Isotec Inc., Miamisburg, Ohio], GlcNAcβOallyl (Compound 40), [Lee et al., Carbohydr. Res., 37:193 (1974)] phosphoenolpyruvate (PEP), and catalytic amounts of Glc-1-P, ATP and UDP. UDP was converted into UTP with pyruvate kinase (PK; EC 2.7.1.40) and PEP, and UTP reacted with Glc-1-P catalyzed by UDPGP to produce UDP-Glc. The byproduct inorganic pyrophosphate (PPi) was decomposed by inorganic pyrophosphatase (PPase; EC 3.6.1.1). With Gal-1-P UT, UDP-Glc reacted with 13C-Gal-1-P, generated from 13C-Gal and ATP in the presence of GK, to give UDP-13C-Gal and Glc-1-P. The 13C-Gal of UDP-13C-Gal was transferred onto the acceptor (GlcNAcβOallyl) by GalT to give [Gal-1-13C]-containing LacNAcβOallyl (Compound 41). The produced UDP was again converted to UTP by a reaction of PK and PEP, which reacted with the released Glc-1-P to regenerate UDP-Glc. Using this multienzyme system, [Gal-1-13C]-LacNAcβOallyl was obtained in 54 percent yield. The same procedure was also used in the preparation of unlabelled LacNAc and analogs. Exemplary analogs 41a-c are illustrated in the scheme.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US07335500B2uspto-grants-2008_02