𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Stereoselective synthesis of stable isotope-labeled L-α-amino acids: Biosynthesis of 2H-, 13C-, and 15N-labeled L-serines

✍ Scribed by John Hanners; Rowena Gibson; Karen Velarde; Judy Hammer; Mark Alvarez; Janet Griego; Clifford J. Unkefer


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

No coin nor oath required. For personal study only.

✦ Synopsis


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 glycine. By starting with the appropriate labeling precursor, we can produce any of the ^2^H, ^13^C and/or ^15^N isotopomers of L‐serine. Using a 5‐L culture, 40–50 millimoles of L‐serine are produced; L‐serine and glycine are recovered from the growth medium and then separated chromatographically.


📜 SIMILAR VOLUMES


Stereoselective synthesis of stable isot
✍ 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
✍ Clifford J. Unkefer; Siegfried N. Lodwig; Louis A. Silks III; John L. Hanners; D 📂 Article 📅 1991 🏛 John Wiley and Sons 🌐 French ⚖ 494 KB

## 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 inco

Stereoselective synthesis of stable isot
✍ 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 15N-, 13C-, and 2H-labeled
✍ Fen-Mei Yao; Sonya L. Palmer; Atmaram D. Khanolkar; Xiaoyu Tian; Jianxin Guo; Al 📂 Article 📅 2003 🏛 John Wiley and Sons 🌐 French ⚖ 145 KB 👁 1 views

## Abstract Four isotopically labeled, metabolically stable analogs of arachidony‐lethanolamide (anandamide), an endogenous cannabinoid ligand, were synthesized via a five‐step reaction sequence starting from arachidonic acid. These stable methanandamide derivatives will serve as probes for studyin

Synthesis of 14C-labeled O-acetyl-L-seri
✍ 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].