The Vespiary

The Hive => Chemistry Discourse => Topic started by: zealot on November 12, 2002, 05:50:00 AM

Title: Biosynthesis of L-tryptophan
Post by: zealot on November 12, 2002, 05:50:00 AM
Hello ladies and gentlemen.
I again ask your help.
I am tormented for a long time with one interesting idea. All of us know a method of reception tryptophan from casein or cottage cheese (rather bad by the way speaking a method, ridiculous yelds it is a lot of difficulties), but it will be possible to find out for all of you unexpectedness that there is much more productive and simple way of reception high pure tryptophan from anthranilic acid: the Biosynthetic way.

The general technique consists in the following:
1. Raise culture of yeast Candida utilis or Candida gidrocarbolatis. This yeast are rather unpretentious in cultivation, very durable.
2. Load a biomass into a reactor (the washing machine in our case since Candida during growth other cultures about sterility suppress is possible to not care especially).
3. Add 5 % alcoholic solution of  anthranilic acid and 50 % a solution of urea, ammonium saltpeters, sulfate of ammonium i.e. ANY available source of nitrogen. Also add these portions each 6 hours till 120 o'clock conducting transformation anthranilic acid. Which turns in L-tryptophan with the contents in a biomass 6 g on 1 litre. 
From 5 g anthranilic acid receive 6 g L-tryptophan 98 %-s' degrees of cleanliness. A total yeld of 95 % in recalculation on anthranilic acid. By itself that in the washing machine it is possible to receive for time up to 200-300 g tryptophan.

And now the most important: I have opportunity to work in microbiological laboratory and to receive superproducers mutants of Candida. To fulfil a technique and to adapt it for « domestic use ».

The unique help which I ask is to help me to find articles with methods of this biosynthesis. I.e. if there will be methods I on anyone shall make superproducers and adapt to a method.
In general now almost all amino acids receive extremely microbiological methods. And tryptophan one of them. And to a method this for the first time have developed already abroad in the Riga institute of microbiology. In 1977 the first plant has been started.
If has interested, write. I shall be glad to hear any responses and comments, but more all, I certainly glad to methods.

From those references, that I have found, but could not pull out:

Evolution of biosynthetic pathway: the tryptophan paradigm.
Crawford Irving
Annu. Rev. Microbiol. Vol.43. Palo Alto (Calif.) 1989. p.567-600

Tryptophan C-methyltransferase of Streptomyces flocculus.
Speedie Marilyn K.
Meth. Enzymol. Vol.142 1987. p.235-242

Tryptophan synthasa from E. coli and Salmonella typhimurium.
Miles Edith Wilson
Meth. Enzymol. Vol.142 1987. p.398-414

Synthesis of tryptophan from horismate: comparative aspects.
Crawford Irving
Meth. Enzymol. Vol.142 1987. p.293-300

V Kostov, B Tsvetkova, S Peskova, S Mutafov, and V Ivanova
[Effect of anthranilic acid on intracellular tryptophan biosynthesis in Candida tropicalis]
Acta Microbiol Bulg, Jan 1979; 4 : 11-7.

LB Lobyreva and EL Ruban
[The effect of sulfur containing amino acids on L-tryptophan biosynthesis from anthranilic acid by yeasts and their accumulation in the biomass]
Izv Akad Nauk SSSR Biol, Jul 1969; 4 : 512-8.

And two last in the Bulgarian language but when to disappear there is no place, …

And still, generally speaking, it is possible to not allocate the moment at all tryptophan from a biomass. If be going to do of it tryptamine it is possible decarboxilated it with the help decarboxilase microorganisms, but it already absolutely other history …



Title: Re: biotransformation
Post by: java on November 12, 2002, 06:31:00 AM
Since you asked about anyone interested , I would be interested in the decarboxyalase procedure , to use on the amino acid Phenylalanine. There is a big entry in this forum on biotransformation  you may or may not know about.  There is a big effort to produce Ephedrine.Your article I found to be informative and very resourceful.  Saludos (Greetings) , from Latin America

Edit:[No 199197  read this on Biotransformation,sorry I couldn't hyper-link it for you.
Title: some more biosynths
Post by: Organikum on November 13, 2002, 04:13:00 AM

- veratraldehyde to (l)3,4-dimethoxyphenylacetyl carbinol

Patent US3338796 (http://l2.espacenet.com/dips/viewer?PN=US3338796&CY=gb&LG=en&DB=EPD)

1964
- phenylacetic acid from phenylalanine

Patent US5420022 (http://l2.espacenet.com/dips/viewer?PN=US5420022&CY=gb&LG=en&DB=EPD)

1995
- optically active arylacetyl carbinols

Patent US1962476 (http://l2.espacenet.com/dips/viewer?PN=US1962476&CY=gb&LG=en&DB=EPD)



an example what may be made of such compounds is shown in the swiss

Patent SW389610 (http://l2.espacenet.com/dips/viewer?PN=SW389610&CY=gb&LG=en&DB=EPD)

where demerol is produced from L-PAC including a nice ring-closing.

many more...



ORGY

now or never
Title: Somebody
Post by: SPISSHAK on November 18, 2002, 09:14:00 AM
Give Zealot an 'excellent' rating for that post he deserves it!
That extraction from casein is a real bear!
And one for organikum that's cool stuff biosynthetic demerol!
WOW!
P.S. Organikum: that Swiss patent comes up unavailable. :(