FMOC phosphorylate Y S T

Tony Houthaeve houthaeve at
Fri Sep 23 10:49:35 EST 1994

In article <lisa-210994143656 at>, lisa at (Lisa Bibbs) writes:
> Are FMOC phosphorylated S Y AND T available?  If so where?  If not, does
> anyone have a good method for synthesizing them or for phosphorylating a
> synthetic peptide.  I'm making a trip to the library this evening, but I
> thought that you guys might have some help for me.
> Thank you
> Lisa

Hi there, 

There are 2 alternative methodologies available for the synthesis of phospho-
peptides. The first one, the one you are referring to, involves the
incorporation of N-a-protected phosphoamino acids in whic hthe side group (PO4)
is protected. When using the FMOC methodology, this restricts only to Y. The
others give beta-elimination problems.
Therefore the strategy to use is called the global phosphorylation strategy.
This involves the post-synthetic phosphorylation of unprotected hydroxylgroups
on the solid support or in the solution. This method has the advantage of
furnishing the amino acids you'd like to. So you just can make a peptide that
you modify let's say the first S, the third one and the second T.
However, this sound easy on paper, it is not straightforwards. The reaction 
itself has to be performed with big molar overexcesses. And especially with 
mutiple sites is dropping in yield.
Additionally, Analysis methods like mass spectrometry are necessary to be 
sure of your endproduct.
Good luck anayway.

Tony Houthaeve

p.s.: by the way Novabiochem is having hand-outs on this strategy.
Probably also other companies in the field.

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