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Preparation of Technical Grade Polyethylene Glycol (PEG) ( M r 20,000)‐ N 6 ‐(2‐Aminoethyl‐NADH by a Procedure Adaptable to Large‐Scale Synthsis
Author(s) -
Buückmann Andreas F.,
Morr Michael,
Kula MariaRegina
Publication year - 1987
Publication title -
biotechnology and applied biochemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 70
eISSN - 1470-8744
pISSN - 0885-4513
DOI - 10.1111/j.1470-8744.1987.tb00407.x
Subject(s) - nad+ kinase , peg ratio , yield (engineering) , chemistry , polyethylene glycol , carbodiimide , ethyleneimine , nuclear chemistry , stereochemistry , organic chemistry , enzyme , materials science , finance , economics , metallurgy , polymer
A procedure for the preparation of technical grade PEG ( M r 20,000)‐ N 6 (2‐aminoethyl)NADH was developed. Using the reaction mixture after the alkylation of NAD by ethyleneimine, containing 25% unreacted NAD, 67% N ( 1 )‐(2‐aminoethyl)‐NAD, and 8% N( I )‐NAD by products, technical grade PEG ( M r , 20,000)‐ N ( 1 )‐(2‐aminoethyl)‐NAD was synthesized by the carbodiimide coupHng method. After chemical reduction to PEG ( M r , 20,000)‐ N 6 ( 1 )‐(2‐aminoethyl)‐NADH and Dimroth rearrangement, technical grade PEG (M, 20,OOO)‐N6‐(2‐aminoethyl)‐ NADH was obtained with an overall yield of 33.5%. By insertion of a cation‐exchange purification step in batch mode after the coupling step and partitioning in PEG‐NADH/Na 2 CO 3 aqueous two‐pbase systems before and after the Dimroth‐rearrangement step, >98% of the uncoupled NAD(H). N ( 1 )‐(2‐aminoethyl)‐NAD(H), and alkylated NAD(H) by‐products could be removed. Because large volumes may be handled easily in these operations, the procedure developed for the preparation of technical grade PEG M r , 20,000)‐ N 6 ‐(2‐aminoethyl)‐NADH now can be adapted to large‐scale synthesis.