Unless we hear anyone claiming otherwise, I suggest it is safe to esterify
histidine without expecting any enantiomerization.
Sincerely yours. NLB.
At 01:59 PM 99/8/12 +1000, you wrote:
>Dear All,
>
>A relatively simple question. We want to make a derivatised Fmoc-histidine
>and are starting by taking L-histidine and methylating the carboxy group to
>protect it. I have used refluxing in HCl and methonol previously to do
>this, but have recently heard that this could lead to racemisation. I
>could imagine this is a problem in the workup where the product is basified
>and extracted, but am not aware of racemisation during the reflux itself.
>Can anyone clarify whether there is a problem here (we are not using dry
>HCl gas as suggested in Bodanszky and Bodanszky.) Thanks for your help.
>
>Colin Barrow
>University of Melbourne
>Australia
>
>
>
N. Leo Benoiton
Department of Biochemistry
University of Ottawa
Ottawa, Ontario, Canada K1H 8M5
Tel: 613 562 5800, Ext. 8216
Fax: 613 562 5440
eMail: benoiton@uottawa.ca