Ethylenediaminetetraacetic Acid → HCID 54350893, compound
Reaction equation
[O:1]=[CH:2][CH:3]([CH2:5][SH:6])[OH:4].N(CCO)(CCO)[CH2:8][CH2:9][OH:10].C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O>>[O:10]=[CH:9][CH2:8][C@@H:2]([C@@H:3]([CH2:5][SH:6])[OH:4])[OH:1]Participants
Conditions
- Temperature
- 0 °C
Procedure
The acceptor aldehyde, 3-thioglyceraldehyde (Compound 3), was prepared by the method of Effenberger. [Effenberger Tetrahedron Lett., 33:5157 (1992)]. DERA (400U) was added to a 10 mL solution containing the acceptor aldehyde (100 mM Compound 3) and donor aldehyde (300 mM acetaldehyde), triethanolamine buffer (100 mM, pH 7.3) and EDTA (1 mM). This reaction is shown in Scheme 1. The resulting solution was stirred in the dark for 2 days under a N2 atmosphere. The reaction was quenched by addition of 2 volumes of acetone and cooling to 0° C. for 20 minutes. The precipitated protein was removed by centrifugation. After removal of the solvent under reduced pressure, a 33 percent yield of Compound 4 was obtained (characterized as 2-deoxy-5-thio-1,3,4-tri-O-acetyl-D-erythro-pentose). Compound 4 was purified from the residue by preparative TLC on silica (methanol/chloroform/hexane, 1:90:10).
Workup
- customThe reaction was quenched by addition of 2 volumes of acetone
- customThe precipitated protein was removed by centrifugation
- customAfter removal of the solvent under reduced pressure
Sources & evidence
- ORD record
- ord-fd907b13486c4e71af8262b14973c3b2
- Source dataset
- uspto-grants-1998_08
- Patent number
- US05795749
Reaction notes
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