Re: PEPTIDE SYNTHESIS

Ron Kasher (ronk@cc.huji.ac.il)
Thu, 12 Mar 1998 11:59:26 +0200 (GMT+0200)

Dear Frank,
It looks like the clour is from impurities, because the peptide should be
white. I suggest to run the product on HPLC diode array, set your detector
wavelength to 215 and 450 nm, and look at the chromatogram you get.

good luck,
Ron KASHER.

On Wed, 11 Mar 1998 mbgbb@seqnet.dl.ac.uk wrote:

>
> Dear ABRF
> I have a question concerning an unusual peptide product. I
> recently made a peptide amide (Rink amide MBHA resin) - sequence:
> QQYNNWPP which upon cleavage with TFA (+ water, phenol,
> triisopropylsilane scavengers) gave a rather dark colour. After the addition of
> cold ether the peptide product went a marvellous shade of bright purple.
> Following dissolution in water the product changed colour once again (a rose
> red colour). I know that colour changes can occur with certain difficult
> peptide sequences but I wondered whether anyone knows the precise reason
> for this colour change. The trp and pro residues were unprotected, the gln and
> asn residues protected with trt, and the tyr residue protected with tBu. I
> suspect that during the cleavage step one of these sidechain protecting groups
> has bound the trp sidechain but I'd like to know more.
> Best wishes
>
> Frank Ward
> King's college London
> Kensington
> UK
>
>
> Dear Frank
>
> I have seen similar things although not quite as colorful! Could be a few
> things:- Your phenol may have degraded (it would be some sort of pink
> colour, probably pale) 2) Some of the linker may have cleaved but not
> very much 3) Some of the trp may have got modified, again it wouldnot
> need much. You could try using Trp (Boc).
>
> Graham Bloomberg
> Dept Biochemistry
> Medical School
> University of Bristol
> Bristol BS8 1TD
> 01179-293205
> G.B.Bloomberg@bristol.ac.uk
>

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
Ron Kasher
Department of Organic Chemistry
The Hebrew University of Jerusalem
Jerusalem, 91904 Israel.

Tel: 972-2-658 6181
Fax: 972-2-658 5345
e-mail: ronk@cc.huji.ac.il