Phosphoenolpyruvate → Udp-Glucose

HRID 429735

반응식

HRID 429735 반응식
C=C(OP(O)(O)=O)C(O)=O.[CH2:11]([OH:26])[C@H:12]1[O:17][CH:16]([O:18][P:19]([OH:22])([OH:21])=[O:20])[C@H:15]([OH:23])[C@@H:14]([OH:24])[C@@H:13]1[OH:25].P(OC[C@H]1O[C@@H](N2C3N=CN=C(N)C=3N=C2)[C@H](O)[C@@H]1O)(OP(OP(O)(O)=O)(O)=O)(=O)O.[CH:58]1[C:64](=[O:65])[NH:63][C:61](=[O:62])[N:60]([C@@H:66]2[O:70][C@H:69]([CH2:71][O:72][P:73](OP(O)(O)=O)([OH:75])=[O:74])[C@@H:68]([OH:81])[C@H:67]2[OH:82])[CH:59]=1.C1C(=O)NC(=O)N([C@@H]2O[C@H](COP(OP(OP(O)(O)=O)(O)=O)(O)=O)[C@@H](O)[C@H]2O)C=1.C([O-])(=O)C(C)=O>>[CH:58]1[C:64](=[O:65])[NH:63][C:61](=[O:62])[N:60]([C@@H:66]2[O:70][C@H:69]([CH2:71][O:72][P:73]([O:20][P:19]([O:18][C@H:16]3[O:17][C@H:12]([CH2:11][OH:26])[C@@H:13]([OH:25])[C@H:14]([OH:24])[C@H:15]3[OH:23])([OH:22])=[O:21])([OH:75])=[O:74])[C@@H:68]([OH:81])[C@H:67]2[OH:82])[CH:59]=1

참가 물질

7

반응물 6

HCID 1005Phosphoenolpyruvate2회HCID 59575'-AtpHCID 6031Uridine Diphosphate2회HCID 6133Uridine 5'-triphosphate2회HCID 107735PyruvateHCID 439165D-glucopyranose 1-phosphate2회

생성물 1

HCID 8629Udp-Glucose

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 및 근거

ORD 기록
ord-7ef1725e757f4319ac96b794e37b58ce
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06319695B1

연결된 노트

불러오는 중…