Acrylamide → 3-(Hydroxymethyl)hexahydro-1H-pyrrolizine-1,2,7-triol

HRID 1493169Notes

Reaction equation

HRID 1493169 reaction equation
C(O)[C@H]1O[C@H](O[C@@H]([C@H](O)[C@@H](O)CO)[C@H](O)CO)[C@H](O)[C@@H](O)[C@@H]1O.[CH2:24]1[C@H:32]([OH:33])[C@H:31]2[N:26]([CH2:27][C@H:28]([OH:36])[C@@H:29]([OH:35])[C@@H:30]2[OH:34])[CH2:25]1.C=CC(N)=O>>[CH2:24]1[C@H:32]([OH:33])[C@H:31]2[N:26]([C@H:27]([CH2:28][OH:36])[C@@H:29]([OH:35])[C@@H:30]2[OH:34])[CH2:25]1

Participants

4

Reactant 3

HCID 6579AcrylamideHCID 54445CastanospermineHCID 493591Maltitol

Product 1

HCID 4426283-(Hydroxymethyl)hexahydro-1H-pyrrolizine-1,2,7-triol

Procedure

Materials. [2-3H] Mannose (15 Ci/mmole) and [6- 3H]galactose (15 Ci/mmole) were purchased from American Radiolabeled Chemicals, Inc. [4,5-3H]Leucine (50 Ci/mmole) was obtained from ICN, pronase was from Calbiochem, and endo-beta-N-acetylglucosaminidase H (Endo H1) was from Miles Scientific. Concanavalin A-Sepharose 4B, maltitol, amyloglucosidase (from Aspergillus niger), beta-glucosidase (from almonds), alpha-galactosidase (from Aspergillus niger), beta-galactosidase (from bovine liver), alpha-mannosidase (from jack bean), and all p-nitrophenyl-glycoside substrates were purchased from Sigma Chemical Company. Beta-Mannosidase was purified from Aspergillus niger as previously described (51). Glucosidase I and glucosidase II were partially purified from mung bean seedlings (50). [3H]Glucose-labeled Glc3Man9GlcNAc-oligosaccharide was isolated from influenza virus-infected MDCK cells labeled with [6-3H]galactose in the presence of castanospermine (52). Tissue culture materials were obtained from Flow Laboratories. Bio-Gel P-4 and Bio-Gel P-2 were purchased from Bio-Rad Laboratories, and Sephadex LH-20 was purchased from Pharmacia Fine Chemicals. Australine was isolated from Castanospermum australe mother liquors by ion exchange chromatography and TLC (53). Castanospermine was isolated from Castanospermum australe mother liquors by crystallization as reported elsewhere (2, 54). All additional chemicals were analytical grade.

Workup

  1. customBeta-Mannosidase was purified from Aspergillus niger
  2. customwere partially purified from mung bean seedlings (50)
  3. customwas isolated from influenza virus-infected MDCK cells

Sources & evidence

ORD record
ord-d919602a0f1a4990b60d009196c37ffe
Source dataset
uspto-grants-1991_06
Patent number
US05021427

Reaction notes

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