672-15-1

Basic information

• Product Name: L-Homoserine
• Synonyms: (S)-(-)-2-AMINO-4-HYDROXYBUTYRIC ACID;(S)-2-AMINO-4-HYDROXYBUTYRIC ACID;L-2-AMINO-4-HYDROXYBUTANOIC ACID;L-2-AMINO-4-HYDROXYBUTYRIC ACID;L-2-AMINO-4-HYDROXYBUTYRIC ACID HYDROCHLORIDE;H-L-HSE-OH;H-HSE-OH;H-HOSER-OH
• CAS NO: 672-15-1
• Molecular Formula: C₄H₉NO₃
• Molecular Weight: 119.12
• EINECS: 211-590-6
• Product Categories: Serine [Ser, S];Unusual Amino Acids;Amino Acids;Amino Acids & Derivatives;amino acids
• Mol File: 672-15-1.mol
• Article Data: 39

Chemical Properties

• Melting Point: 203 °C (dec.)(lit.)
• Boiling Point: 222.38°C (rough estimate)
• Flash Point: 176.8 °C
• Appearance: White to light yellow/Crystalline Powder
• Density: 1.3126 (rough estimate)
• Refractive Index: 1.4183 (estimate)
• Storage Temp.: Store at RT.
• Solubility: 1100g/l
• PKA: 2.71(at 25℃)
• Water Solubility: 1100 g/L (30 ºC)
• Merck: 14,4739
• BRN: 1721681
• CAS DataBase Reference: L-Homoserine(CAS DataBase Reference)
• NIST Chemistry Reference: L-Homoserine(672-15-1)
• EPA Substance Registry System: L-Homoserine(672-15-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 24/25-44-35-26-28-7-4-3/9
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 672-15-1(Hazardous Substances Data)

Usage

Description

L-Homoserine, a variant of serine with an additional carbon on its side chain, is the L-enantiomer of homoserine. It is a white to light yellow crystalline powder and has a role as a human, algal, Saccharomyces cerevisiae, and Escherichia coli metabolite. It is an enantiomer of D-homoserine and a tautomer of L-homoserine zwitterion.

Uses

Used in Biosynthesis:
L-Homoserine is used as a precursor in the biosynthesis of essential amino acids such as methionine, threonine, and isoleucine, which are crucial for various biological processes and protein synthesis.
Used in Neurotransmitter Analysis:
L-Homoserine is used as an internal standard for neurotransmitter analysis, helping to ensure accurate and reliable measurements in the study of neurotransmitters and their roles in the nervous system.
Used in Amino Acids Quantification:
L-Homoserine is also utilized as an internal standard for amino acids quantification, aiding in the accurate determination of amino acid concentrations in various samples, which is vital for understanding metabolic processes and nutritional requirements.

Synthesis Reference(s)

Journal of the American Chemical Society, 80, p. 3147, 1958 DOI: 10.1021/ja01545a057The Journal of Organic Chemistry, 24, p. 1794, 1959 DOI: 10.1021/jo01093a610

Biochem/physiol Actions

L-Homoserine is synthesized by deoxidation process, catalysed by homoserine dehydrogenase. This is one of the steps in the synthesis of L-threonine. The carbon flux in in bacteria such as E. coli is maintained by this reaction.

Purification Methods

Likely impurities are N-chloroacetyl-L-homoserine, N-chloroacetyl-D-homoserine, L-homoserine, homoserine lactone, homoserine anhydride (formed in strong solutions of homoserine if slightly acidic). It cyclises to the lactone in strongly acidic solution. It crystallises from water by adding 9 volumes of EtOH. [Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 2612-2616 1961, Beilstein 4 IV 3187.]

InChI:InChI=1/C4H9NO3/c5-3(1-2-6)4(7)8/h3,6H,1-2,5H2,(H,7,8)/t3-/m0/s1

Synthetic route

Isopropyl (2S)-N-(trifluoroacetyl)homoserine (159487-41-9) → L-homoserine (672-15-1)

Conditions	Yield
With ethanol	95%
With potassium hydroxide In ethanol for 2h;	95%

(3S)-(3-amino-3-carboxypropyl)dimethylsulfonium iodide (3493-11-6) → L-homoserine (672-15-1)

Conditions	Yield
With water; sodium hydrogencarbonate pH=2 - 5; Reflux;	92%
With sodium hydrogencarbonate In water pH=3 - 6; Inert atmosphere; Schlenk technique; Reflux;	92%
With sodium hydrogencarbonate In water at 140℃; for 0.5h;	69%

L-homoserine lactone hydrochloride (2185-03-7) → L-homoserine (672-15-1)

Conditions	Yield
With triethylamine In water for 2h; Ambient temperature;	82%

2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-1-N-(4-L-aspartoyl)-2-deoxy-β-D-glucopyranosylamine (29625-73-8) → L-homoserine (672-15-1) + N,N'-diacetylchitobiosamine (102039-77-0) + 1-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-amino-1,2-dideoxy-D-glucitol (118943-00-3) + 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-1-amino-1,2-dideoxy-D-glucitol (119009-35-7)

Conditions	Yield
With lithium hydroxide; lithium borohydride; trilithium citrate In water; tert-butyl alcohol at 45℃; for 5h; Yield given;	A 80% B 72% C n/a D n/a

2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-1-N-(4-L-aspartoyl)-2-deoxy-β-D-glucopyranosylamine (29625-73-8) → L-homoserine (672-15-1) + N,N'-diacetylchitobiosamine (102039-77-0) + 1-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-amino-1,2-dideoxy-D-glucitol (118943-00-3) + 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-1-amino-1,2-dideoxy-D-glucitol (119009-35-7) + β-D-GlcpNAc(1->4)-D-GlcNAc-ol (29886-32-6)

Conditions	Yield
With lithium hydroxide; lithium borohydride; trilithium citrate In water; tert-butyl alcohol at 45℃; for 5h; Product distribution;	A 80% B 72% C n/a D n/a E 5%

2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-1-N-(4-L-aspartoyl)-2-deoxy-β-D-glucopyranosylamine (29625-73-8) → L-homoserine (672-15-1) + N,N'-diacetylchitobiosamine (102039-77-0) + 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-1-amino-1,2-dideoxy-D-glucitol (119009-35-7) + β-D-GlcpNAc(1->4)-D-GlcNAc-ol (29886-32-6)

Conditions	Yield
With lithium hydroxide; lithium borohydride; trilithium citrate In water; tert-butyl alcohol at 45℃; for 5h;	A 80% B 72% C n/a D 5%

L-methionine (63-68-3) → L-homoserine (672-15-1)

Conditions	Yield
With water; methyl iodide at 20℃; for 24h; Inert atmosphere; Reflux;	74%
Stage #1: L-methionine With methyl iodide In water for 24h; Inert atmosphere; Stage #2: With potassium hydrogencarbonate for 10h; pH=3 - 6; Reflux; Stage #3: With hydrogenchloride In water pH=5 - 6;	74%
Stage #1: L-methionine With methyl iodide In methanol; water for 48h; Stage #2: With sodium hydrogencarbonate In methanol; water for 15h; Reflux;	62%
With sodium hydrogencarbonate; methyl iodide In methanol; water for 12h; Reflux;

(S)-tert-butyl 1-(furan-2-yl)-3-hydroxypropylcarbamate (1149755-80-5) → L-homoserine (672-15-1)

Conditions	Yield
Stage #1: (S)-tert-butyl 1-(furan-2-yl)-3-hydroxypropylcarbamate With ozone In methanol at -78℃; for 0.166667h; Stage #2: With dimethylsulfide In methanol at 20℃; for 12h; Stage #3: With hydrogenchloride In 1,4-dioxane at 0 - 20℃;	62%

L-methionine (63-68-3) + ptaquiloside (87625-62-5) → L-homoserine (672-15-1) + 2(R)-pterosin B (34175-96-7) + (R)-2,5,7-Trimethyl-6-(2-methylsulfanyl-ethyl)-indan-1-one (114751-11-0) + (S)-2-Amino-4-methylsulfanyl-butyric acid 2-((R)-2,4,6-trimethyl-3-oxo-indan-5-yl)-ethyl ester (114751-12-1)

Conditions	Yield
With sodium hydroxide; Amberlite CG 50 (H form) In water; acetone at 37℃; for 12h; 1.) pH: 9.2;	A 10% B 26% C 12% D 4%

2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-1-N-(4-L-aspartoyl)-2-deoxy-β-D-glucopyranosylamine (29625-73-8) → L-homoserine (672-15-1) + L-Aspartic acid (56-84-8) + β-D-GlcpNAc(1->4)-D-GlcNAc-ol (29886-32-6)

Conditions	Yield
With sodium hydroxide; sodium tetrahydroborate	A 15% B 3% C 20%

L-homoserine lactone (2185-02-6) → L-homoserine (672-15-1)

Conditions	Yield
In alkalischen und in verduennten neutralen wss. Loesungen;
With water; sodium hydrogencarbonate at 100℃; for 24h;	8.8 g

N-chloroacetyl of racemic homoserine lacton (879008-07-8) → L-homoserine (672-15-1)

Conditions	Yield
Enzymatische Herstellung;

(+)-β-methyl-L-aspartate hydrochloride (16856-13-6) → L-homoserine (672-15-1)

Conditions	Yield
With lithium borohydride In tetrahydrofuran

Pyoverdine Pa → L-homoserine (672-15-1)

Conditions	Yield
hydrolysis;

S-methyl-L-methionine hydrobromide (33515-32-1) → L-homoserine (672-15-1)

Conditions	Yield
With sodium hydrogencarbonate In methanol; water for 20h; Heating; Yield given;

tert-butyl (2S,5S)-2-(tert-butyl)-5-(2-hydroxyethyl)-3-methyl-4-oxo-1-imidazolidinecarboxylate (123052-97-1) → L-homoserine (672-15-1)

Conditions	Yield
With hydrogenchloride; Dowex 50-WX8; acetic acid; trifluoroacetic acid 1.) CH2Cl2, 30 min, 0 deg C; 12 h, room temperature; 2.) 100-105 deg C, toluene, water, 36 h; Yield given. Multistep reaction;

formaldehyd (50-00-0) + (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide (96293-17-3, 105024-93-9, 105112-33-2) + glycine (56-40-6) → D-Serine (312-84-5) + L-serin (56-45-1) + L-homoserine (672-15-1)

Conditions	Yield
With nickel nitrate; water; sodium methylate; triethylamine 1.) MeOH, 2 h, 50 deg C; 2.) MeOH, 50 deg C; Yield given. Multistep reaction. Yields of byproduct given;

Cbz-Ser(Bn)-OH → L-homoserine (672-15-1) + O-benzylserine

Conditions	Yield
With hydrogen; hydrogen In methanol for 20h; Ambient temperature;	A 60 % Spectr. B 40 % Spectr.

formic acid (64-18-6) + L-methionine (63-68-3) → L-homoserine (672-15-1) + L-Aspartic acid (56-84-8) + L-methionine sulfoxide (3226-65-1) + L-glutamic acid (56-86-0) + L-methionine sulfone (7314-32-1) + L-homocysteic acid (14857-77-3)

Conditions	Yield
With hydrogen; oxygen In water at 40 - 50℃; Product distribution; Mechanism; A flame from a burner fed with H2-O2 mixtures of different compositions were blown onto the surface of an aq. solution of pH=3;

L-methionine (63-68-3) → L-2-aminobutyric acid (1492-24-6) + L-homoserine (672-15-1) + L-Aspartic acid (56-84-8) + L-methionine sulfoxide (3226-65-1) + L-methionine sulfone (7314-32-1) + L-homocysteic acid (14857-77-3)

Conditions	Yield
With hydrogen; oxygen In water at 40 - 50℃; Product distribution; Mechanism; A flame from a burner fed with H2-O2 mixtures of different compositions were blown onto the surface of an aq. solution of pH=3;

L-methionine (63-68-3) → L-homoserine (672-15-1) + L-Aspartic acid (56-84-8) + L-methionine sulfone (7314-32-1) + L-homocysteic acid (14857-77-3)

Conditions	Yield
With formic acid; hydrogen; oxygen In water at 40 - 50℃; a flame from a burner fed with H2+O2 was blown to the surface of an aq. solution; H2:O2=50:50; Further byproducts given;

L-methionine (63-68-3) → L-homoserine (672-15-1) + L-Aspartic acid (56-84-8) + L-methionine sulfoxide (3226-65-1) + L-methionine sulfone (7314-32-1) + (S)-aspartate β-semialdehyde (498-20-4, 2338-03-6, 15106-57-7, 23632-91-9) + L-homocysteic acid (14857-77-3)

Conditions	Yield
With hydrogen; oxygen In water Product distribution; various sulfur-containing amino acids under different reaction conditions;

L-homoserine lactone (2185-02-6) + strong acid aqueous solution → L-homoserine (672-15-1)

Conditions	Yield
Equilibrium constant;

L-homoserine lactone (2185-02-6) → L-homoserine (672-15-1) + (3S,6S)-3,6-bis-<2-hydroxy-ethyl>-piperazine-2,5-dione

Conditions	Yield
In konzentrierten und in schwach sauren wss. Loesungen;

L-α-amino-γ-butyrolactone hydrobromide → L-homoserine (672-15-1)

Conditions	Yield
With water; silver(l) oxide at 20℃;

L-canaline → L-homoserine (672-15-1)

Conditions	Yield
With methanol; platinum durch Hydrogenolyse;

L-S-methylmethionine sulfonium chloride (1115-84-0, 3493-12-7, 41844-44-4, 71267-08-8) → dimethylsulfide (75-18-3) + L-homoserine (672-15-1)

Conditions	Yield
With sodium hydroxide at 100℃; Kinetics;

C10H17NO6 → L-homoserine (672-15-1)

Conditions	Yield
With hydrogenchloride; water at 100℃; for 1h;

C16H31NO4 (137100-14-2) → lauric acid (143-07-7) + L-homoserine (672-15-1)

Conditions	Yield
With AHSL acylase Enzymatic reaction;

methanol (67-56-1) + L-homoserine (672-15-1) → (S)-4-hydroxy-1-methoxy-1-oxobutan-2-aminium chloride

Conditions	Yield
With thionyl chloride at 0 - 20℃; for 12.5h;	100%

formaldehyd (50-00-0) + L-homoserine (672-15-1) → (S)-1,3-oxazinane-4-carboxylic acid

Conditions	Yield
With sodium hydroxide at 2 - 10℃;	100%

L-homoserine (672-15-1) → L-homoserine lactone hydrochloride (2185-03-7)

Conditions	Yield
With hydrogenchloride In water for 0.25h;	99%
With hydrogenchloride for 5h; Reflux;	99%
With hydrogenchloride a) reflux, 3 h, b) RT, 16 h;	94%

ethanol (64-17-5) + L-homoserine (672-15-1) → (S)-4-chloro-2-aminobutanoic acid ethyl ester hydrochloride

Conditions	Yield
With thionyl chloride	98%
With thionyl chloride at 0 - 20℃; for 80h; Heating / reflux;	92%

L-homoserine (672-15-1) + [(p-methylphenyl)sulfonylmethyl]isonitrile (38622-91-2, 36635-61-7) + isobutyraldehyde (78-84-2) → 3-methyl-2-(2-oxo-tetrahydro-furan-3-ylamino)-N-(toluene-4-sulfonylmethyl)-butyramide

Conditions	Yield
With 2,2,2-trifluoroethanol at 30 - 40℃; for 94h;	97%

L-homoserine (672-15-1) + urea (57-13-6) → (S)-5-(2-hydroxyethyl)imidazolidin-2,4-dione

Conditions	Yield
Stage #1: L-homoserine; urea In water at 100℃; for 8h; Stage #2: With hydrogenchloride In water at 90℃; for 6h;	96%

L-homoserine (672-15-1) + di-tert-butyl dicarbonate (24424-99-5) → L-2-(tert-butyloxycarbonylamino)-4-hydroxybutyric acid (41088-86-2)

Conditions	Yield
With sodium carbonate In acetone at 19℃; for 8.3h; Temperature; Cooling with ice;	95%
With sodium hydroxide In 1,4-dioxane; water at 0 - 25℃; for 24.5h;	93%
With sodium hydroxide In water; acetone at 0 - 20℃; for 4h; Reagent/catalyst;	93%

L-homoserine (672-15-1) → (2S)-2-amino-4-bromo-butanoic acid

Conditions	Yield
With hydrogen bromide; acetic acid at 80℃; for 6h; Sealed tube;	95%
With hydrogen bromide; acetic acid at 80℃; for 5h;

L-homoserine (672-15-1) + benzyl chloroformate (501-53-1) → N-benzyloxycarbonyl-(L)-homoserine (35677-88-4)

Conditions	Yield
With sodium carbonate In acetone at 18℃; for 14.6h; Temperature; Cooling with ice;	94%
With sodium hydrogencarbonate In water for 3h;	92%
With sodium hydrogencarbonate at 20℃; for 24h;	89%

L-homoserine (672-15-1) + tert-butylisonitrile (119072-55-8, 7188-38-7) + butyraldehyde (123-72-8) → 2-(2-oxo-tetrahydro-furan-3-ylamino)-pentanoic acid tert-butylamide

Conditions	Yield
With 2,2,2-trifluoroethanol at 30 - 40℃; for 18h;	93%

L-homoserine (672-15-1) + C25H26N2O2 (1445869-56-6) + nickel(II) acetate tetrahydrate (6018-89-9) → C29H31N3NiO4

Conditions	Yield
With potassium carbonate In ethanol at 60 - 70℃; diastereoselective reaction;	93%

L-homoserine (672-15-1) → (S)-cis-3,6-bis-(2-hydroxy-ethyl)-piperazine-2,5-dione (28814-72-4, 46318-21-2, 50975-79-6)

Conditions	Yield
In ethylene glycol at 150℃; for 36h;	93%

L-homoserine (672-15-1) + [(p-methylphenyl)sulfonylmethyl]isonitrile (38622-91-2, 36635-61-7) + pivalaldehyde (630-19-3) → 3,3-dimethyl-2-(2-oxo-tetrahydro-furan-3-ylamino)-N-(toluene-4-sulfonylmethyl)-butyramide

Conditions	Yield
With 2,2,2-trifluoroethanol at 30 - 40℃; for 94h;	92%

L-homoserine (672-15-1) + tert-butyldimethylsilyl chloride (18162-48-6) → (2S)-amino-4-(tert-butyldimethylsilanyloxy)butanoic acid (474023-97-7)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 20℃; for 16.0833h;	92%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 20℃; for 16.0833h;	92%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 20℃; for 16.0833h;	92%

L-homoserine (672-15-1) + 4-nitrobenzyl chloroformate (4457-32-3) → N-p-nitrobenzyloxycarbonyl-(2S)-homoserine

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water for 0.75h; Ambient temperature;	91%

L-homoserine (672-15-1) + benzyloxycarbonyl-O-benzyl-L-tyrosine 1-succinimidyl ester (52773-66-7) → C28H30N2O7 (1161754-51-3)

Conditions	Yield
With potassium hydrogencarbonate In tetrahydrofuran at 20℃;	90%

[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 (52462-29-0) + L-homoserine (672-15-1) → [Ru(η6-p-cymene)(κ2N,O-L-homoserinato)Cl]

Conditions	Yield
With sodium hydroxide In methanol at 20℃; for 3.5h; diastereoselective reaction;	90%

L-homoserine (672-15-1) + benzenesulfonyl chloride (98-09-9) → N-(phenylsulfonyl)-L-homoserine (558481-13-3)

Conditions	Yield
With sodium hydroxide at 20℃; for 7h;	89%

L-homoserine (672-15-1) → L-homoserine O-sulfate (19794-26-4)

Conditions	Yield
With sulfuric acid at 20℃; for 3.5h;	88%

L-homoserine (672-15-1) + Fmoc-OSu → Nα-(Fluoren-9-ylmethoxycarbonyl)-L-homoserine (172525-85-8)

Conditions	Yield
With sodium hydrogencarbonate In water; acetone Cooling;	88%

L-homoserine (672-15-1) + tert-butyl pyridin-2-yl carbonate (89985-91-1) → L-2-(tert-butyloxycarbonylamino)-4-hydroxybutyric acid (41088-86-2)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water at 0℃; for 24h;	88%

Cyclohexyl isocyanide (931-53-3) + L-homoserine (672-15-1) + cyclohexanone (108-94-1) → 1-((S)-2-Oxo-tetrahydro-furan-3-ylamino)-cyclohexanecarboxylic acid cyclohexylamide

Conditions	Yield
With 2,2,2-trifluoroethanol at 30 - 40℃; for 48h;	87%

L-homoserine (672-15-1) → γ-Cl-Abu (39537-41-2)

Conditions	Yield
With hydrogenchloride; tetrabutylammomium bromide In water at 80℃; for 9h; Sealed tube;	87%

L-homoserine (672-15-1) + allyl bromide (106-95-6) + Allyl chloroformate (2937-50-0) → L-homoserine (143966-59-0)

Conditions	Yield
Stage #1: L-homoserine; Allyl chloroformate With sodium carbonate In water; acetonitrile at 20℃; Stage #2: allyl bromide With sodium hydrogencarbonate In N,N-dimethyl-formamide	86%

L-homoserine (672-15-1) + tetradecanoyl chloride (112-64-1) → N-tetradecanoyl-L-homoserine

Conditions	Yield
With potassium hydrogencarbonate In diethyl ether; water for 20h; Ambient temperature;	85%

L-homoserine (672-15-1) + methyl iodide (74-88-4) → L-N,N,N-trimethylhomoserine

Conditions	Yield
With potassium hydrogencarbonate In methanol for 48h; Ambient temperature;	85%

L-homoserine (672-15-1) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → Nα-(Fluoren-9-ylmethoxycarbonyl)-L-homoserine (172525-85-8)

Conditions	Yield
With sodium hydrogencarbonate In acetonitrile	85%
With sodium hydrogencarbonate
With sodium carbonate In 1,4-dioxane; water

L-homoserine (672-15-1) → (2S)-2-amino-4-bromobutanoic acid hydrobromide (15159-65-6)

Conditions	Yield
With hydrogen bromide at 75 - 80℃; for 5h;	85%
With hydrogen bromide; acetic acid at 75 - 80℃; for 5h; Autoclave;	85%
With hydrogen bromide; acetic acid at 50℃; for 12h; Sealed tube;	78%

Upstream product

• 2185-02-6 L-homoserine lactone 
• 879008-07-8 N-chloroacetyl of racemic homoserine lacton 
• 16856-13-6 (+)-β-methyl-L-aspartate hydrochloride 
• 63-68-3 L-methionine 
• 87625-62-5 ptaquiloside 
• 29625-73-8 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-1-N-(4-L-aspartoyl)-2-deoxy-β-D-glucopyranosylamine 
• 33515-32-1 S-methyl-L-methionine hydrobromide 
• 123052-97-1 tert-butyl (2S,5S)-2-(tert-butyl)-5-(2-hydroxyethyl)-3-methyl-4-oxo-1-imidazolidinecarboxylate 
• 50-00-0 formaldehyd 
• 96293-17-3 (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide 
• 56-40-6 glycine 
• 159487-41-9 Isopropyl (2S)-N-(trifluoroacetyl)homoserine 
• 3493-11-6 (3S)-(3-amino-3-carboxypropyl)dimethylsulfonium iodide 
• 2185-03-7 L-homoserine lactone hydrochloride 

Downstream Products

• 600-18-0 2-Oxobutyric acid 
• 41088-87-3 N-benzoyl-L-homoserine 
• 4096-48-4 O-oxalylhomoserine 
• 23809-78-1 (S)-2-Benzyloxycarbonylamino-4-hydroxy-butyric acid 4-nitro-benzyl ester 
• 116786-66-4 Methyl 4,6-Dideoxy-4-<(S)-2,4-dihydroxybutanamido>-α-D-mannopyranoside 
• 31982-10-2 meso-homolanthione 
• 31982-10-2 L-homolanthionine 
• 62-49-7 choline 
• 108865-87-8 Hexadecanoic acid (R)-2-[((S)-3-amino-3-carboxy-propoxy)-hydroxy-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl ester 
• 108824-18-6 (E)-Octadec-9-enoic acid (R)-2-[((S)-3-amino-3-carboxy-propoxy)-hydroxy-phosphoryloxy]-1-((E)-octadec-9-enoyloxymethyl)-ethyl ester 
• 107862-71-5 (9E,12E)-Octadeca-9,12-dienoic acid (R)-2-[((S)-3-amino-3-carboxy-propoxy)-hydroxy-phosphoryloxy]-1-((9E,12E)-octadeca-9,12-dienoyloxymethyl)-ethyl ester 
• 35677-88-4 N-benzyloxycarbonyl-(L)-homoserine 
• 62445-25-4 (L)-2,4-dihydroxybutyrate 
• 52079-23-9 (3S)-3-hydroxydihydrofuran-2(3H)-one 

Relevant articles and documents

Synthesis and delivery of a stable phosphorylated ubiquitin probe to study ubiquitin conjugation in mitophagy

Protein post-translational modifications are involved in essentially all aspects of cellular signaling. Their dynamic nature and the difficulties in installing them using enzymatic approaches limits their direct study in human cells. Reported herein is the first synthesis, delivery and cellular study of a stable phosphoubiquitin probe. Our results compare Parkin's substrate preference during mitophagyviadirect visualization of a phosphorylated ubiquitin probe in the cellular environment.

Design, synthesis, and evaluation of compounds capable of reducing Pseudomonas aeruginosa virulence

Anti-virulence approaches in the treatment of Pseudomonas aeruginosa (PA)-induced infections have shown clinical potential in multiple in vitro and in vivo studies. However, development of these compounds is limited by several factors, including the lack of molecules capable of penetrating the membrane of gram-negative organisms. Here, we report the identification of novel structurally diverse compounds that inhibit PqsR and LasR-based signaling and diminish virulence factor production and biofilm growth in two clinically relevant strains of P. aeruginosa. It is the first report where potential anti-virulent agents were evaluated for inhibition of several virulence factors of PA. Finally, co-treatment with these inhibitors significantly reduced the production of virulence factors induced by the presence of sub-inhibitory levels of ciprofloxacin. Further, we have analyzed the drug-likeness profile of designed compounds using quantitative estimates of drug-likeness (QED) and confirmed their potential as hit molecules for further development.

Discovery of new A- and B-type laxaphycins with synergistic anticancer activity

Two new cyclic lipopeptides termed laxaphycins B4 (1) and A2 (2) were discovered from a collection of the marine cyanobacterium Hormothamnion enteromorphoides, along with the known compound laxaphycin A. The planar structures were solved based on a combined interpretation of 1D and 2D NMR data and mass spectral data. The absolute configurations of the subunits were determined by chiral LC-MS analysis of the hydrolysates, advanced Marfey's analysis and 1D and 2D ROESY experiments. Consistent with similar findings on other laxaphycin A- and B-type peptides, laxaphycin B4 (1) showed antiproliferative effects against human colon cancer HCT116 cells with IC50 of 1.7 μM, while laxaphycins A and A2 (2) exhibited weak activities. The two major compounds isolated from the sample, laxaphycins A and B4, were shown to act synergistically to inhibit the growth of HCT116 colorectal cancer cells.