31771-40-1

Usage

Uses

Used in Nutritional Supplements:
L-threonine is utilized as a nutritional supplement to support individuals with specific dietary restrictions or those requiring additional support for tissue growth and repair, such as athletes undergoing intense physical training.
Used in Pharmaceutical Applications:
In the pharmaceutical industry, L-threonine is used as an active pharmaceutical ingredient for the development of medications targeting various health conditions, leveraging its role in protein synthesis and metabolic processes.
Used in Food and Beverage Industry:
L-threonine is employed as a food additive to enhance the nutritional content of products, particularly for those designed to meet the needs of specific consumer groups, such as individuals following specialized diets or with unique nutritional requirements.
Used in Cosmetics and Personal Care Products:
In the cosmetics and personal care industry, L-threonine may be used in formulations to support skin health and repair, capitalizing on its role in collagen and elastin synthesis, which are crucial for maintaining skin elasticity and structure.

Synthetic route

(R)-2-hydroxy-4-phthalimidobutyric acid → (R)-β-hydroxy-4-aminobutyric acid (31771-40-1)

Conditions	Yield
With hydrazine hydrate In ethanol for 2h; Heating;	73%

γ-phthalimidoimino-α-hydroxybutyric acid (40732-91-0) → (R)-β-hydroxy-4-aminobutyric acid (31771-40-1)

Conditions	Yield
(i) (racemate resolution using dehydroabiethylamine), (ii) aq. HCl; Multistep reaction;

(R)-4-benzyloxycarbonylamino-2-hydroxybutanoic acid (42491-77-0) → (R)-β-hydroxy-4-aminobutyric acid (31771-40-1)

Conditions	Yield
With hydrogen; palladium on activated charcoal

4-amino-n-butyric acid (56-12-2) → (S)-4-amino-2-hydroxybutanoic acid (3938-83-8, 13477-53-7, 31771-40-1, 40371-51-5) + (R)-β-hydroxy-4-aminobutyric acid (31771-40-1)

Conditions	Yield
With wildtype taurine dioxygenase Enzymatic reaction; enantioselective reaction;	A n/a B n/a

4-amino-n-butyric acid (56-12-2) → (R)-β-hydroxy-4-aminobutyric acid (31771-40-1)

Conditions	Yield
With taurine dioxygenase F206Y mutant Enzymatic reaction; enantioselective reaction;	n/a

(R)-β-hydroxy-4-aminobutyric acid (31771-40-1) + 9-fluorenylmethyl N-succinimidyl carbonate (102774-86-7) → (2R)-4-[(9-fluorenylmethoxy)carbonylamino]-2-hydroxybutyric acid (905857-47-8)

Conditions	Yield
With sodium hydrogencarbonate In 1,2-dimethoxyethane; water at 20℃; for 0.2625h;	95.8%

(R)-β-hydroxy-4-aminobutyric acid (31771-40-1) + (R)-1-bromo-5-(3-carboxy-3-hydroxypropylamino)-2,4-dinitrobenzene (261375-47-7) → (R,R)-1,5-bis(3-carboxy-3-hydroxypropylamino)-2,4-dinitrobenzene (261375-48-8)

Conditions	Yield
With sodium carbonate In acetone for 20h; Substitution; Heating;	80.6%

(R)-β-hydroxy-4-aminobutyric acid (31771-40-1) + 3-bromo-4-nitrotoluene (40385-54-4) → (R)-2-Hydroxy-4-(5-methyl-2-nitro-phenylamino)-butyric acid (188753-45-9)

Conditions	Yield
With sodium ethanolate In ethanol; N,N-dimethyl-formamide for 16h; Heating;	56%

(R)-β-hydroxy-4-aminobutyric acid (31771-40-1) → (3R)-3-hydroxy-2-pyrrolidinone (77510-50-0)

Conditions	Yield
With hydrogenchloride In ethanol for 48h; Ambient temperature;	35%
With chloro-trimethyl-silane; (Me3Si)2SiNH; trifluoroacetic acid 1) xylene, heat, 2) THF, H2O; Yield given. Multistep reaction;

1,5-dibromo-2,4-dinitrobenzene (24239-82-5) + (R)-β-hydroxy-4-aminobutyric acid (31771-40-1) → (R)-1-bromo-5-(3-carboxy-3-hydroxypropylamino)-2,4-dinitrobenzene (261375-47-7)

Conditions	Yield
With sodium carbonate In acetone for 22h; Substitution; Heating;

(R)-β-hydroxy-4-aminobutyric acid (31771-40-1) + 4-methoxy-benzoyl chloride (100-07-2) → (R)-4-(p-methoxybenzoylamino)-2-hydroxybutyric acid (78340-49-5)

Conditions	Yield
In water

(R)-β-hydroxy-4-aminobutyric acid (31771-40-1) → (R)-3-((trimethylsilyl)oxy)pyrrolidin-2-one

Conditions	Yield
With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane In o-xylene

(R)-β-hydroxy-4-aminobutyric acid (31771-40-1) → (R)-4-amino-1,2-butanediol (82267-24-1)

Conditions	Yield
With lithium borohydride; chloro-trimethyl-silane In tetrahydrofuran Inert atmosphere;

Upstream product

• 1758-80-1 L-2,4-diaminobutyrate 
• 57229-74-0 (S)-2-hydroxysuccinamic acid 
• 40732-91-0 γ-phthalimidoimino-α-hydroxybutyric acid 
• 40371-50-4 S-4-benzyloxycarbonylamino-2-hydroxybutyric acid 
• 56-12-2 4-amino-n-butyric acid 
• 42491-77-0 (R)-4-benzyloxycarbonylamino-2-hydroxybutanoic acid 
• 31701-91-4 (R)-2-hydroxy-4-phthalimidobutyric acid 

Downstream Products

• 34368-52-0 (S)-3-hydroxypyrrolidin-2-one 
• 111607-75-1 (S)-hydroxy-3 phenylacetyl-1 pyrrolidinone-2 
• 40371-50-4 S-4-benzyloxycarbonylamino-2-hydroxybutyric acid 
• 188753-46-0 (S)-2-Hydroxy-4-(5-methyl-2-nitro-phenylamino)-butyric acid 
• 207305-60-0 (S)-4-[(tert-butoxycarbonyl)amino]-2-hydroxybutanoic acid 
• 850397-64-7 4-Benzyloxycarbonylamino-2S-hydroxy butyric acid ethyl ester 
• 149137-92-8 (2S)-4-(p-nitrobenzyloxycarbonyl)-amino-2-hydroxybutyric acid 
• 48172-10-7 (+)-(2S)-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-hydroxybutanoic acid 
• 1221492-53-0 N,N'-bis(benzyloxycarbonyl)-2-(S)-hydroxy-4-guanidino-butyric acid 
• 1455086-97-1 2-(S)-hydroxy-4-[(4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]butyric acid 
• 1455088-71-7 (S)-4-(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxamido)-2-hydroxybutanoic acid 
• 77510-50-0 (3R)-3-hydroxy-2-pyrrolidinone 
• 188753-45-9 (R)-2-Hydroxy-4-(5-methyl-2-nitro-phenylamino)-butyric acid 
• 261375-47-7 (R)-1-bromo-5-(3-carboxy-3-hydroxypropylamino)-2,4-dinitrobenzene 

Relevant academic research and scientific papers

α-Hydroxylation of Carboxylic Acids Catalyzed by Taurine Dioxygenase

Enzymes still have a limited application scope in synthetic organic chemistry. To expand this, different strategies exist that range from the de novo design of enzymes to the exploitation of the catalytic capabilities of known enzymes by converting different substrates; denoted as substrate promiscuity. We harnessed the synthetic potential offered by the taurine dioxygenase (TauD) from Escherichia coli (E. coli) by studying its promiscuous catalytic properties in the hydroxylation of carboxylic acid substrates. TauD showed high selectivities in the hydroxylation reaction but reduced levels of activity (26 % conversion, >96 % ee). We enhanced the enzyme substrate scope and improved the conversions for the tested substrates by introducing a point mutation at position 206 (F206Y). The conversions of the improved catalyst increased by at least 140 % compared to that of the wild-type enzyme. The number of carboxylic acids that accepted by the enzyme variant doubled from four to eight carboxylic acids.

Enantioselective Syntheses of (S)- and (R)-3-Hydroxypyrrolidin-2-ones via Lactate Dehydrogenase Catalysed Reductions of 4-Benzyloxycarbonylamino-2-oxobutanoic Acid

The first examples of the BS- and SE-lactate dehydrogenase catalysed reductions of an α-keto acid incorporating a nitrogen containing function in the side chain are described: (S)- and (R)-benzyloxycarbonylamino-2-hydroxybutanoic acids were prepared in good yield and excellent enantioselectivities and were converted to the (S)- and (R)-3-hydroxypyrrolidin-2-ones respectively.

Hydroxylations microbiologiques de pyrrolidinones-2 (note de laboratoire)

Microbial hydroxylations of various pyrrolidin-2 ones, especially N-acylated, with Beauveria sulfurescens have been carried out.The regioselectivity depends on the nature of the substituent on the nitrogen atom and the hydroxylation may occur at position 3,4 or 5 of the heterocycle.Hydroxylations at position 3 or 4 occur with low enantioselectivity.