𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Stereoselective synthesis of stable isotope-labeled L-α-amino acids: Chemomicrobiological synthesis of L-[β-13C]-, L-[2′-13C]-, and L-[1′15N]tryptophan

✍ Scribed by Clifford J. Unkefer; Siegfried N. Lodwig; Louis A. Silks III; John L. Hanners; Deborah S. Ehler; Rowena Gibson

Publisher
John Wiley and Sons
Year
1991
Tongue
French
Weight
494 KB
Volume
29
Category
Article
ISSN
0022-2135

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

We have developed a stereospecific chemomicrobiological synthesis of labeled tryptophan. L‐[3‐^13^C]Serine, [1‐^15^N]‐ and [2‐^13^C]indole were used as precursors for the synthesis of L‐[β‐^13^C]‐, L‐[1′‐^15^N]‐, and L‐[2′‐^13^C]tryptophan, respectively. The labeled precursors were incorporated quantitatively into tryptophan using a strain of E. coli engineered to overproduce tryptophan synthase. Labeled indoles were prepared by the base‐promoted cyclization of appropriately labeled N‐formyl‐o‐toluide; serine was prepared biosynthetically as described previously.

📜 SIMILAR VOLUMES

Stereoselective synthesis of stable isot
Stereoselective synthesis of stable isotope-labeled L-α-amino acids: Chemomicrobiological synthesis of 13C- and 2H-labeled L-cysteine
✍ Clifford J. Unkefer; John L. Hanners; Deborah S. Ehler 📂 Article 📅 1991 🏛 John Wiley and Sons 🌐 French ⚖ 284 KB

## Abstract Tryptophan synthase catalyzes the nucleophilic replacement of the hydroxyl group at C‐3 of L‐serine. This enzyme can use benzyl mercaptan as a nucleophile in the conversion of serine to S‐benzyl‐L‐cysteine which is deblocked by treatment with sodium in liquid ammonia to yield L‐cysteine

Stereoselective synthesis of stable isot
Stereoselective synthesis of stable isotope-labeled L-α-amino acids: Biosynthesis of 2H-, 13C-, and 15N-labeled L-serines
✍ John Hanners; Rowena Gibson; Karen Velarde; Judy Hammer; Mark Alvarez; Janet Gri 📂 Article 📅 1991 🏛 John Wiley and Sons 🌐 French ⚖ 460 KB

## Abstract We have developed a stereospecific biosynthesis of ^13^C‐ and ^15^N‐labeled L‐serine which involves the serine‐type methylotroph __Methylobacterium extorquens__ AM1. In this biosynthesis, C‐3 of serine is derived from methanol while C‐2, C‐1 and the α‐amino group are derived from glycin

Stereoselective synthesis of stable isot
Stereoselective synthesis of stable isotope-labeled L-α-amino acids: Electrophilic amination of Oppolzer's acyl sultams in the synthesis of L-[15N]alanine, L-[15N]valine, L-[15N]leucine, L-[15N]phenylalanine and L-[1-13C, 15N]valine
✍ Siegfried N. Lodwig; Clifford J. Unkefer 📂 Article 📅 1996 🏛 John Wiley and Sons 🌐 French ⚖ 475 KB 👁 1 views

Using 1 -chloro-l-[~~N]nitrosocyclohexane, we have prepared five L-[a-'SN]arnino acids. The stereoselective electophillic hydroxyamination of (S)-acylbornane-l0,2-suftams, followed by ZnO/H+ reduction, and alkaline cleavage of the chiral auxiliary, gave the amino acids in 97.2-99.5 % e.e. By starti

Synthesis of D,L-[2-15N,5-13C]glutamic a
Synthesis of D,L-[2-15N,5-13C]glutamic acid
✍ John C. Laiuppa; David M. Lemaster 📂 Article 📅 1993 🏛 John Wiley and Sons 🌐 French ⚖ 281 KB

## Abstract A one‐pot procedure is described for the synthesis of D,L‐[2‐^15^N,5‐^13^C]glutamic acid from 2‐bromo‐4–butyrolactone utilizing potassium ^15^N‐phthalimide and potassium ^13^C‐cyanide as label sources. Following a two column purification procedure, the final product is obtained in 38% y

Synthesis of 14C-labeled O-acetyl-L-seri
Synthesis of 14C-labeled O-acetyl-L-serine, O-benzoyl-L-serine, β-N-phenyl-L-asparagine, benzyl glycinate, and α-dimethylaminoisobutyric acid
✍ William E. Adam; Edward W. Snook; Thomas J. Curphey 📂 Article 📅 1981 🏛 John Wiley and Sons 🌐 French ⚖ 264 KB

## Abstract Syntheses and analyses are described for β‐N‐phenyl [^14^C(U)]‐L‐asparagine, O‐acetyl [1‐^14^C]‐L‐serine, O‐benzoyl [7‐^14^C]‐L‐serine, benzyl[7‐^14^C]glycinate __p__‐toluenesulfonate, benzyl glycinate[1‐^14^C] __p__‐toluenesulfonate, and α‐dimethylaminoisobutyric acid[1‐^14^C].