The synthesis of succinyl-AAPF-pnitroanilide is described by DelMar
et al., in Anal. Biochem., 99, 316-320 (1979). It is a useful substrate
for chymotrypsin and subtilisin.
Chris Halkides
>Sometime ago I replied to another (similar) enquiry with the following
>reference for the prep of CBZ-nitro-Arg-pNA
>
>N Nishi, S Tokura and J Noguchi, Bull Chem Soc Japan 43, 2900-2907 (1970)
>
>This work is in English and from memory worked well for me in the late 70's
>with BOC- and CBZ-Args provided the nitrophenylisocyanate was good stuff
>and the HMPA had been freshly distilled ie that same morning!
>
>Dave Harding
>
>
>At 01:25 7/24/1998 +0400, Rodionov wrote:
>>Dear Jane and Leo,
>>
>>As far as I know the problems with coupling to p-nitroaniline are even more
>>serious than you expect: no reaction is observed when standard coupling
>>procedures are employed.
>>In my opinion even HATU may fail with this amine. DMAP catalysis may be
>>more helpful in this case.
>>
>>However, an old but efficient synthetic approach for p-nitoanilides exists.
>>The procedure is based on reaction of p-nitrophenylisocyanate with
>>COOH-group of protected peptide or amino acid followed by carbon dioxide
>>elimination.
>>I have no exact reference for the related original paper at hand but I am
>>sure that this old peptide chemistry (including detailed protocols) is well
>>documented in:
>>
>>Synthese von Peptiden. (Muller, E. Ed.) In: Houben Weil's Methoden der
>>Organichen Chemie, Stuttgart: Thieme 1974, Bd.15, Teil 1-2.
>>
>>A native German-speaking friend may be of tremendous help in getting
>>necessary information from this great book!
>>
>>Best wishes,
>> Igor Rodionov
>>
>>Laboratory Of Peptide Chemistry
>>Branch of Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry
>>Pushchino, Moscow Region
>>142292, Russian Federation
>>E-mail: <rodionov@fibkh.serpukhov.su> or <Igor_Rodionov@iname.com>
>>Fax: (0967)-79-05-27
>>Phones: (0967) 73 54 42; private: (0967) 73 58 26
>>
>>
>>
>>
>>
>-----------------------------------------------------------------------
>David RK Harding
>Centre for Separation Science
>Institute of Fundamental Sciences
>Massey University
>Palmerston North
>New Zealand
>
>phone 64 6 350-5016 (work) 64 6 356-2837 (home)
>fax 64 6 354-2140 (work)
Christopher Halkides
Dept. of Chemistry, UNCW
601 S. College Road
Wilmington, NC 28403-3297
(910) 962-7427