Related Experiment Video
Updated: Jan 28, 2026

The Modular Design and Production of an Intelligent Robot Based on a Closed-Loop Control Strategy
Published on: October 14, 2017
Design strategy for serine hydroxymethyltransferase probes based on retro-aldol-type reaction
Hiroshi Nonaka1, Yuki Nakanishi2, Satoshi Kuno2
1Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-8656, Japan. hnonaka@chembio.t.u-tokyo.ac.jp.
Abstract:
Serine hydroxymethyltransferase (SHMT) is an enzyme that catalyzes the reaction that converts serine to glycine. It plays an important role in one-carbon metabolism. Recently, SHMT has been shown to be associated with various diseases. Therefore, SHMT has attracted attention as a biomarker and drug target. However, the development of molecular probes responsive to SHMT has not yet been realized. This is because SHMT catalyzes an essential yet simple reaction; thus, the substrates that can be accepted into the active site of SHMT are limited. Here, we focus on the SHMT-catalyzed retro-aldol reaction rather than the canonical serine-glycine conversion and succeed in developing fluorescent and 19F NMR molecular probes. Taking advantage of the facile and direct detection of SHMT, the developed fluorescent probe is used in the high-throughput screening for human SHMT inhibitors, and two hit compounds are obtained.
Related Concept Videos
C–C Bond Cleavage: Retro-Aldol Reaction
In the first step, as depicted in Figure 1, the base deprotonates the β-hydroxy ketone at the hydroxyl group to form an alkoxide ion.
Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction
Base-Catalyzed Aldol Addition Reaction
Crossed Aldol Reaction Using Weak Bases
Intramolecular Aldol Reaction
Crossed Aldol Reactions: Overview

