𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Synthesis of enantiomerically pure α-[14C]methyl-L-tryptophan

✍ Scribed by S. Mzengeza; T.K. Venkatachalam; S. Rajagopal; M. Diksic

Publisher
Elsevier Science
Year
1993
Tongue
English
Weight
423 KB
Volume
44
Category
Article
ISSN
0969-8043

No coin nor oath required. For personal study only.

✦ Synopsis

A practical method for the preparation of large amounts of enantiomerically pure alpha-[14C]methyl-L-tryptophan using the enzymatic resolution of the corresponding D,L-methyl ester is reported. The radiolabelled alpha-methyl group was introduced using the alpha-methylation of the lithium enolate of the Schiff base of L-tryptophan methyl ester. Hydrolysis of the Schiff base with 1N HCl provided the D,L-methyl ester of alpha-[14C]methyl tryptophan. Enantioselective enzymatic hydrolysis of the L-methyl ester by alpha-chymotrypsin gave the enantiomerically pure alpha-[14C]methyl-L-tryptophan. The overall yield of this preparation was 33%.

📜 SIMILAR VOLUMES

Synthesis of α-[14C]methyl and α-[3H]met
Synthesis of α-[14C]methyl and α-[3H]methyl-L-tryptophan
✍ T. K. Venkatachalam; S. Mzengeza; M. Diksic 📂 Article 📅 1993 🏛 John Wiley and Sons 🌐 French ⚖ 383 KB

## Abstract The title compounds were synthesized starting from dimethyl (2S,3aR,8aS)‐(+)‐8‐(phenylsulfonyl)hexahydrophyrrolo[2,3‐b]indole‐1,2‐dicarboxylate. This compound on treatment with LDA followed by reaction with [^14^C]methyl iodide or [^3^H]methyl iodide gave the methyl substituted derivati

Synthesis of enantiomerically pure carbo
Synthesis of enantiomerically pure carbocyclic α-l-isomeric homonucleosides
✍ F. Girard; C. Demaison; M.-G. Lee; L.A. Agrofoglio 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 384 KB

Synthesis of hitherto unknown carbocyclic a-L-isomeric homonucleosides (Sa-b, 9a.b) is described. The key intermediate 6 was synthesized from the known compound 1 as a chiral starting material. Construction of the heteroo,clic moiety around the amino group of 6 afforded carbocyclic Or-Lisomeric 2 ',

Synthesis of [14C]-l-tryptophan and [14C
Synthesis of [14C]-l-tryptophan and [14C]-5′-hydroxy-l-tryptophan labeled in the carboxyl group
✍ E. Boroda; R. Kański; M. Kańska 📂 Article 📅 2003 🏛 John Wiley and Sons 🌐 French ⚖ 88 KB

## Abstract The synthesis of selectively ^14^C‐labeled l‐tryptophan and its derivative 5‐hydroxy‐l‐tryptophan using chemical and multienzymatic methods is reported. The mixture containing [1‐^14^C[‐dl‐alanine, indole or 5‐hydroxyindole has been converted to [1‐^14^C]‐l‐tryptophan or 5′‐hydroxy‐[1‐^

ChemInform Abstract: Synthesis of Enanti
ChemInform Abstract: Synthesis of Enantiomerically Pure Carbocyclic α-L-Isomeric Homonucleosides.
✍ F. GIRARD; C. DEMAISON; M.-G. LEE; L. A. AGROFOGLIO 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 39 KB 👁 1 views

## Synthesis of Enantiomerically Pure Carbocyclic α-L-Isomeric Homonucleosides. -The synthesis of hitherto unknown carbocyclic 2',3'-dideoxyhomonucleosides (X)-(XIII) starting from the known chiral lactone (I) is accomplished. The transformation of the (R)-hydroxy group in derivative (IV) to the