Delving into the Latest Updates on D-tagatose with Synapse

Overview

Basic Info

Drug Type

Small molecule drug

Synonyms

(3S,4S,5R)-1,3,4,5,6-pentahydroxyhexan-2-one, D-lyxo-hex-2-ulose, D-lyxo-hexulose

+ [4]

Target-

Mechanism

Iron chelating agents

Therapeutic Areas

Nervous System DiseasesCongenital DisordersEndocrinology and Metabolic Disease+ [1]

Active Indication

Prader-Willi SyndromeDiabetes Mellitus, Type 2Hyperlipoproteinemia Type I

Inactive Indication-

Originator Organization

Chromadex Corp.

Active Organization

Biospherics.net, Inc.Chromadex Corp.

Inactive Organization

Dominari Holdings, Inc.

Drug Highest PhasePhase 3

First Approval Date-

RegulationOrphan Drug (US)

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Structure/Sequence

Molecular FormulaC6H12O6

InChIKeyBJHIKXHVCXFQLS-PQLUHFTBSA-N

CAS Registry87-81-0

Worldwide almost 40% of the adult population is overweight (including >10% obese), and more than 350 million children (up to the age of 19) are overweight. Overweight and obesity are significant problems and important risk factors for several lifestyle-related diseases, such as cardiovascular disease, certain cancers, non-alcoholic fatty liver disease (NAFLD) and type 2 diabetes (T2D). Excessive consumption of glucose/sucrose is a major contributor to overweight and obesity. Alternative, low-calorie sweeteners could reduce daily energy intake and thus slow down the development of these conditions and related diseases. (3S,4S,5R)-1,3,4,5,6-pentahydroxy-hexan-2-one is a sweetener that may be suitable for use as a sugar substitute; it is only partially digested in the small intestine and as a result has a lower energy density than more traditional sweeteners such as sucrose. However, it is not yet known to what extent (3S,4S,5R)-1,3,4,5,6-pentahydroxy-hexan-2-one is used in the body and then excreted.
The aim of this study is to measure the metabolic utilization (the 'mass balance') of a single dose of 14C-labelled (3S,4S,5R)-1,3,4,5,6-pentahydroxy-hexan-2-one and AMS technology. Based on clinical data of excretion (urine and faeces) and CO2 production (expired air), the mass balance can be derived. These generated results will be used to map the metabolic pathways (3S,4S,5R)-1,3,4,5,6-pentahydroxy-hexan-2-one undergoes during the digestion process. In addition, it will provide insight into the use of AMS technology to investigate the relationship between diet and health.

Start Date05 Feb 2024

Sponsor / Collaborator

Wageningen University

[+2]

JPRN-UMIN000026233

/ CompletedNot ApplicableIIT

A study of the effects on oral bacteria with D-Tagatose chewing gum - A study with D-Tagatose chewing gum

Start Date06 Aug 2015

Sponsor / Collaborator-

NCT00961662

/ CompletedPhase 2

Dose Ranging Effects of Three Low-doses of Naturlose™ (Tagatose) on Glycemic Control and Safety of Naturlose™ (Tagatose) Over Six Months in Subjects With Mild Type 2 Diabetes Mellitus Under Control With Diet and Exercise.

This study is a six-month, prospective, randomized, multicenter, single- blind, controlled clinical study to evaluate the effect of three low-doses of Naturlose (Tagatose) on glycemic control and safety in subjects with Type 2 diabetes under diet control and exercise. The subjects were randomized in one of the 3 arms receiving 2.5, 5 or 7.5 gm of Tagatose.

Start Date01 Feb 2008

Sponsor / Collaborator

University of Kentucky

100 Clinical Results associated with D-tagatose

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100 Translational Medicine associated with D-tagatose

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100 Patents (Medical) associated with D-tagatose

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877

Literatures (Medical) associated with D-tagatose

15 Jan 2025·Journal of Agricultural and Food Chemistry

Thermostability Enhancement of Tagatose 4-Epimerase through Protein Engineering and Whole-Cell Immobilization

Article

Author: Guo, Xuehong ; Liu, Zhanzhi ; Wu, Jing ; Xu, Ying

d-Tagatose, a rare sugar endowed with a low-calorie property, superior taste quality, and probiotic functionality, has garnered significant research attention. However, the prevailing biological production methods relying on β-galactosidase and l-arabinose isomerase face challenges including high cost and suboptimal conversion efficiency. Consequently, it is of great research significance to find efficient alternative routes for d-tagatose synthesis. Previously, Thermotoga petrophila tagaturonate 3-epimerase was modified to function as tagatose 4-epimerase (T4E) enabling the direct conversion of d-fructose to d-tagatose. In this study, T4E was further engineered through directed evolution, specifically targeting the enhancement of its thermostability for application. This endeavor yielded promising T4E variants with superiority over those of the original enzyme. T4E I430P exhibits a half-life (t_1/2) at 70 °C that is 1.83-fold that of T4E, with an increased melting temperature (T_m) of 5.1 °C compared to T4E. Additionally, T4E G90S/T272A/I430P demonstrated a 21.4% increase in specific activity compared to T4E. At 70 °C, its t_1/2 was 1.69-fold that of T4E, and its T_m is 2.9 °C higher than T4E. Furthermore, whole-cell immobilization integrating these engineered T4E variants into a robust biocatalytic system was employed. This innovative approach not only underscores the practical feasibility of modifying enzymes through directed evolution but also establishes a foundation for the cost-effective, large-scale production of d-tagatose.

01 Jan 2025·Radiotherapy and Oncology

EGCG protects intestines of mice and pelvic cancer patients against radiation injury via the gut microbiota/D-tagatose/AMPK axis

Article

Author: Li, Ming ; Yang, Yinyin ; Li, Mingyue ; Tang, Fengling ; Wang, Difan ; Liu, Chengzhi ; Xie, Liwei ; Gu, Xuhao ; Tian, Ye ; Zhu, Ruiqiu ; Lu, Haiyan ; Guo, Liangsheng ; Cai, Shang

BACKGROUND AND PURPOSERadiation-induced intestinal injury (RIII) compromises the clinical utility of pelvic radiotherapy (RT). We aimed to explore the protective effect and underlying mechanism of (-)-epigallocatechin-3-gallate (EGCG) on RIII.MATERIALS AND METHODSWe evaluated the protective effect of EGCG on intestine in RIII mouse model and pelvic cancer patients, while explored the underlying mechanism through (1) 16S rRNA sequencing, (2) metabolomic profiles, (3) fresh sterile fecal filtrate (SFF) transplantation, and (4) transcriptome sequencing.RESULTSEGCG efficiently prevented RIII in mouse, as reflected by improved survival, alleviated intestinal structure damage, promoted intestinal regeneration, and ameliorated gut microbiota dysbiosis. Prophylactic EGCG intervention reduced the severity of RIII in patients receiving pelvic RT. Mechanistically, the protective effect of EGCG could be transferred to other mice by SFF transplantation. EGCG enriched gut microbiota-derived metabolite D-tagatose, and oral administration of D-tagatose reproduced the radio-protective effect of EGCG via activating AMPK.CONCLUSIONOral EGCG may be a promising strategy for preventing RIII clinically, and warrant further investigation in prospective randomized phase III trials.

01 Jan 2025·Applied Biochemistry and Biotechnology

Development and Characterization of a Tunable Metal–Organic Framework (MOF) for the Synthesis of a Rare Sugar D-Tagatose

Article

Author: Mittal, Divya ; Bhatiya, Simran ; Dhiman, Rishu ; Yadav, Sudesh Kumar ; Rai, Shushil Kumar

D-tagatose is a valuable rare sugar with potential health benefits such as antiobesity, low-calorie, prebiotic, and anticancer. However, its production is mainly depending on chemical or enzymatic catalysis. Herein, a cobalt-based metal-organic framework (MOF) was developed at room temperature in an aqueous system using a self-assembly method. The L-arabinose isomerase (L-AI) was immobilized into this unique MOF by an in situ encapsulation process. The morphology and structural aspects of the MOF preparations were characterized by different analytical techniques such as scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), confocal laser scanning microscopy (CLSM), Fourier transform infrared spectroscopy (FT-IR), and X-Ray diffraction (XRD). Moreover, thermogravimetric analysis (TGA) suggested the high thermal stability of the L-AI@MOF. Significantly, the immobilized catalyst exhibited enhanced catalytic efficiency (k_cat/K_m) of 3.22 mM^-1 s^-1 and improved turnover number (k_cat) of 57.32 s^-1. The L-AI@MOF efficiently catalyzes the synthesis of D-tagatose from D-galactose up to the equilibrium level (~ 50%) of isomerization in heterogeneous catalysis. Interestingly, L-AI@MOF was found stable and reusable for more than five cycles without the requirement of additional metal ions during catalysis. Thus, L-AI stabilized in the MOF system demonstrated a higher catalytic activity and potential guidance for the sustainable synthesis of rare sugar D-tagatose.

100 Deals associated with D-tagatose

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External Link

KEGG	Wiki	ATC	Drug Bank
-	D-tagatose	-	DB04936

R&D Status

10 top R&D records.

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Indication	Highest Phase	Country/Location	Organization	Date
Diabetes Mellitus, Type 2	Phase 3	-	Chromadex Corp.	-
Hyperlipoproteinemia Type I	Phase 3	-	Chromadex Corp.	-
Prader-Willi Syndrome	Phase 3	-	Chromadex Corp.	-

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Clinical Result

Indication

Phase

Evaluation

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Study	Phase	Population	Analyzed Enrollment	Group	Results	Evaluation	Publication Date


NCT00955747 (NEET, CTgov)	Phase 3	Diabetes Mellitus, Type 2	494	Sugar Substitute Splenda (Sugar Substitute Splenda)	ujcoaftnoa(jzjvvlqqsp) = kjiqvavwqc nocnmvdntw (dnzmxtusnn, pqeifmnufm - vikdkehvms) View more	-	19 Nov 2014
				Tagatose (Tagatose)	ujcoaftnoa(jzjvvlqqsp) = rnlonafhbn nocnmvdntw (dnzmxtusnn, boowmbdale - qukhklelzk) View more
NCT00961662 (CTgov)	Phase 2	Diabetes Mellitus, Type 2	161	D-Tagatose (2.5 Active)	vplbphilyt(jwunwjweif) = swgdqpowsq exhwhxugrg (dgqwuontit, xronjshvdm - jjvldwjfca) View more	-	06 Nov 2014
				D-Tagatose (5.0 Mid Dose)	vplbphilyt(jwunwjweif) = oqcccioylx exhwhxugrg (dgqwuontit, idphxfbcgf - izctxxsiva) View more