1119-34-2

Basic information

• Product Name: 2-Amino-5-guanidinovaleric acid monohydrochloride
• Synonyms: argininemonohydrochloride;argivene;detoxargin;hydrochloride,l-arginin;L-1-Amino-4-guanidovalericacidhydrochloride;L-Argininiumchloride;levargin;L-Guanidineaminovalericacidhydrochloride
• CAS NO: 1119-34-2
• Molecular Formula: C₆H₁₅N₄O₂*Cl
• Molecular Weight: 210.66
• EINECS: 214-275-1
• Product Categories: chiral;Amino Acid Derivatives;Amino Acids 13C, 2H, 15N;alpha-Amino Acids;Amino Acids;Biochemistry;for Resolution of Acids;Optical Resolution;Synthetic Organic Chemistry;Nutritional Supplements;L-Amino Acids;Amino Acids;Amino Acids, Peptides and Proteins;Life Sciences Standards;Amino Acids & Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals;PRILOSEC;amino
• Mol File: 1119-34-2.mol
• Article Data: 6

Chemical Properties

• Melting Point: 226-230 °C(lit.)
• Boiling Point: 409.1 °C at 760 mmHg
• Flash Point: 201.2 °C
• Appearance: white/powder
• Density: 1.42
• Vapor Pressure: 7.7E-08mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: H2O: 100 mg/mL
• PKA: 1[at 20 ℃]
• Water Solubility: Soluble in water. Slightly soluble in hot alcohol.
• Sensitive: Hygroscopic
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,780
• BRN: 3631658
• CAS DataBase Reference: 2-Amino-5-guanidinovaleric acid monohydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-5-guanidinovaleric acid monohydrochloride(1119-34-2)
• EPA Substance Registry System: 2-Amino-5-guanidinovaleric acid monohydrochloride(1119-34-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 37-36/38-36/37/38-20/21/22
• Safety Statements: 37/39-26-24/25-36
• WGK Germany: 2
• RTECS: CF1995500
• F: 3-10
• TSCA: Yes
• Hazardous Substances Data: 1119-34-2(Hazardous Substances Data)

Usage

Chemical Properties

White crystalline powder

Uses

Different sources of media describe the Uses of 1119-34-2 differently. You can refer to the following data:
1. gastric acid depressant
2. An essential amino acid for human development. Precursor for nitric oxide. Ammonia detoxicant (hepatic failure); diagnostic aid (pituitary function).
3. L-Arginine monohydrochloride is used in the treatment of heart and circulatory diseases. It is a precursor of nitric oxide synthesis that induces vasodilation in vivo, there by relaxing blood vessels. It is also used in the treatment of angina and other cardiovascular problems. It is an important intermediate in the urea cycle and involved in the detoxification of nitrogenous wastes. It is commonly used in cell culture media and drug development.

Brand name

R-Gene 10 (Pharmacia & Upjohn).

Biochem/physiol Actions

L-Arginine is considered as a semi essential amino acid. In most mammals including humans, L-Arginine synthesis occurs through intestinal-renal axis, from glutamine, glutamate and proline. Abnormal levels of L-Arginine is associated with the development of kidney and cardiovascular disease. L-arginine is found to decrease fat mass and visceral adiposity.

Safety Profile

Moderately toxic by intraperitoneal route. Mildly toxic by ingestion. An experimental teratogen. When heated to decomposition it emits very toxic fumes of NOx and HCl.

Purification Methods

A likely impurity is ornithine. Crystallise the salt from H2O at pH 5-7, by adding EtOH to 80% (v/v). [Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 p 1841 1961, Beilstein 4 IV 2649.]

InChI:InChI=1/C6H14N4O2.ClH/c7-4(5(11)12)2-1-3-10-6(8)9;/h4H,1-3,7H2,(H,11,12)(H4,8,9,10);1H

Synthetic route

micropeptin MZ845 (914606-75-0) → D-glyceric acid (473-81-4, 600-19-1, 6000-40-4, 28305-26-2) + l-glutamic acid hydrochloride (138-15-8) + L-arginine hydrochloride (1119-34-2) + N-methyl-L-phenylalanine hydrochloride (66866-67-9) + L-isoleucine hydrochloride (17694-98-3) + L-threonine methyl ester hydrochloride (60143-52-4, 71264-40-9, 82650-07-5, 97347-46-1, 100157-61-7)

Conditions	Yield
Stage #1: micropeptin MZ845 With Jones reagent In acetone at 0℃; for 0.166667h; Stage #2: With hydrogenchloride; water at 110℃; for 16h; Sealed glass bomb;

micropeptin MZ845 (914606-75-0) → D-glyceric acid (473-81-4, 600-19-1, 6000-40-4, 28305-26-2) + L-arginine hydrochloride (1119-34-2) + N-methyl-L-phenylalanine hydrochloride (66866-67-9) + L-isoleucine hydrochloride (17694-98-3) + L-threonine methyl ester hydrochloride (60143-52-4, 71264-40-9, 82650-07-5, 97347-46-1, 100157-61-7)

Conditions	Yield
With hydrogenchloride; water at 110℃; for 16h; Sealed glass bomb;

micropeptin MZ859 (1207348-70-6) → D-glyceric acid (473-81-4, 600-19-1, 6000-40-4, 28305-26-2) + l-glutamic acid hydrochloride (138-15-8) + L-arginine hydrochloride (1119-34-2) + N-methyl-L-phenylalanine hydrochloride (66866-67-9) + L-isoleucine hydrochloride (17694-98-3) + L-threonine methyl ester hydrochloride (60143-52-4, 71264-40-9, 82650-07-5, 97347-46-1, 100157-61-7)

Conditions	Yield
Stage #1: micropeptin MZ859 With Jones reagent In acetone at 0℃; for 0.166667h; Stage #2: With hydrogenchloride; water at 110℃; for 16h; Sealed glass bomb;

micropeptin MZ859 (1207348-70-6) → D-glyceric acid (473-81-4, 600-19-1, 6000-40-4, 28305-26-2) + L-arginine hydrochloride (1119-34-2) + N-methyl-L-phenylalanine hydrochloride (66866-67-9) + L-isoleucine hydrochloride (17694-98-3) + L-threonine methyl ester hydrochloride (60143-52-4, 71264-40-9, 82650-07-5, 97347-46-1, 100157-61-7)

Conditions	Yield
With hydrogenchloride; water at 110℃; for 16h; Sealed glass bomb;

micropeptin MZ939A (1207348-72-8) → D-glyceric acid (473-81-4, 600-19-1, 6000-40-4, 28305-26-2) + l-glutamic acid hydrochloride (138-15-8) + L-arginine hydrochloride (1119-34-2) + N-methyl-L-phenylalanine hydrochloride (66866-67-9) + L-isoleucine hydrochloride (17694-98-3) + L-threonine methyl ester hydrochloride (60143-52-4, 71264-40-9, 82650-07-5, 97347-46-1, 100157-61-7)

Conditions	Yield
Stage #1: micropeptin MZ939A With Jones reagent In acetone at 0℃; for 0.166667h; Stage #2: With hydrogenchloride; water at 110℃; for 16h; Sealed glass bomb;

micropeptin MZ939A (1207348-72-8) → D-glyceric acid (473-81-4, 600-19-1, 6000-40-4, 28305-26-2) + L-arginine hydrochloride (1119-34-2) + N-methyl-L-phenylalanine hydrochloride (66866-67-9) + L-isoleucine hydrochloride (17694-98-3) + L-threonine methyl ester hydrochloride (60143-52-4, 71264-40-9, 82650-07-5, 97347-46-1, 100157-61-7)

Conditions	Yield
With hydrogenchloride; water at 110℃; for 16h; Sealed glass bomb;

micropeptin MZ925 (1207348-74-0) → D-glyceric acid (473-81-4, 600-19-1, 6000-40-4, 28305-26-2) + l-glutamic acid hydrochloride (138-15-8) + L-arginine hydrochloride (1119-34-2) + N-methyl-L-phenylalanine hydrochloride (66866-67-9) + L-isoleucine hydrochloride (17694-98-3) + L-threonine methyl ester hydrochloride (60143-52-4, 71264-40-9, 82650-07-5, 97347-46-1, 100157-61-7)

Conditions	Yield
Stage #1: micropeptin MZ925 With Jones reagent In acetone at 0℃; for 0.166667h; Stage #2: With hydrogenchloride; water at 110℃; for 16h; Sealed glass bomb;

micropeptin MZ925 (1207348-74-0) → D-glyceric acid (473-81-4, 600-19-1, 6000-40-4, 28305-26-2) + L-arginine hydrochloride (1119-34-2) + N-methyl-L-phenylalanine hydrochloride (66866-67-9) + L-isoleucine hydrochloride (17694-98-3) + L-threonine methyl ester hydrochloride (60143-52-4, 71264-40-9, 82650-07-5, 97347-46-1, 100157-61-7)

Conditions	Yield
With hydrogenchloride; water at 110℃; for 16h; Sealed glass bomb;

micropeptin MZ939B (1207348-76-2) → D-glyceric acid (473-81-4, 600-19-1, 6000-40-4, 28305-26-2) + l-glutamic acid hydrochloride (138-15-8) + L-arginine hydrochloride (1119-34-2) + N-methyl-L-phenylalanine hydrochloride (66866-67-9) + L-isoleucine hydrochloride (17694-98-3) + L-threonine methyl ester hydrochloride (60143-52-4, 71264-40-9, 82650-07-5, 97347-46-1, 100157-61-7)

Conditions	Yield
Stage #1: micropeptin MZ939B With Jones reagent In acetone at 0℃; for 0.166667h; Stage #2: With hydrogenchloride; water at 110℃; for 16h; Sealed glass bomb;

micropeptin MZ939B (1207348-76-2) → D-glyceric acid (473-81-4, 600-19-1, 6000-40-4, 28305-26-2) + L-arginine hydrochloride (1119-34-2) + N-methyl-L-phenylalanine hydrochloride (66866-67-9) + L-isoleucine hydrochloride (17694-98-3) + L-threonine methyl ester hydrochloride (60143-52-4, 71264-40-9, 82650-07-5, 97347-46-1, 100157-61-7)

Conditions	Yield
With hydrogenchloride; water at 110℃; for 16h; Sealed glass bomb;

micropeptin MZ1019 (1207348-78-4) → D-glyceric acid (473-81-4, 600-19-1, 6000-40-4, 28305-26-2) + l-glutamic acid hydrochloride (138-15-8) + L-arginine hydrochloride (1119-34-2) + N-methyl-L-phenylalanine hydrochloride (66866-67-9) + L-isoleucine hydrochloride (17694-98-3) + L-threonine methyl ester hydrochloride (60143-52-4, 71264-40-9, 82650-07-5, 97347-46-1, 100157-61-7)

Conditions	Yield
Stage #1: micropeptin MZ1019 With Jones reagent In acetone at 0℃; for 0.166667h; Stage #2: With hydrogenchloride; water at 110℃; for 16h; Sealed glass bomb;

micropeptin MZ1019 (1207348-78-4) → D-glyceric acid (473-81-4, 600-19-1, 6000-40-4, 28305-26-2) + L-arginine hydrochloride (1119-34-2) + N-methyl-L-phenylalanine hydrochloride (66866-67-9) + L-isoleucine hydrochloride (17694-98-3) + L-threonine methyl ester hydrochloride (60143-52-4, 71264-40-9, 82650-07-5, 97347-46-1, 100157-61-7)

Conditions	Yield
With hydrogenchloride; water at 110℃; for 16h; Sealed glass bomb;

micropeptin MZ771 (1207348-80-8) → l-glutamic acid hydrochloride (138-15-8) + L-arginine hydrochloride (1119-34-2) + N-methyl-L-phenylalanine hydrochloride (66866-67-9) + L-isoleucine hydrochloride (17694-98-3) + L-threonine methyl ester hydrochloride (60143-52-4, 71264-40-9, 82650-07-5, 97347-46-1, 100157-61-7)

Conditions	Yield
Stage #1: micropeptin MZ771 With Jones reagent In acetone at 0℃; for 0.166667h; Stage #2: With hydrogenchloride; water at 110℃; for 16h; Sealed glass bomb;

micropeptin MZ771 (1207348-80-8) → L-arginine hydrochloride (1119-34-2) + N-methyl-L-phenylalanine hydrochloride (66866-67-9) + L-isoleucine hydrochloride (17694-98-3) + L-threonine methyl ester hydrochloride (60143-52-4, 71264-40-9, 82650-07-5, 97347-46-1, 100157-61-7)

Conditions	Yield
With hydrogenchloride; water at 110℃; for 16h; Sealed glass bomb;

L-arginine (74-79-3) → L-arginine hydrochloride (1119-34-2)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane
With hydrogenchloride In 1,4-dioxane

di-tert-butyl dicarbonate (24424-99-5) + L-arginine hydrochloride (1119-34-2) → t-butyloxycarbonyl-L-arginine (13726-76-6)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane at 20℃; for 21h;	92%

L-arginine hydrochloride (1119-34-2) → N-(3-cyanopropyl)-guanidine monohydrochloride

Conditions	Yield
With ammonium bromide In water for 15h; Electrochemical reaction;	91%

L-arginine hydrochloride (1119-34-2) + Tosyl isocyanate (4083-64-1) → α-4-toluenesulfonylureido-L-arginine hydrochloride

Conditions	Yield
at 4℃;	90%

C22H23N3O10 (1043921-27-2) + L-arginine hydrochloride (1119-34-2) → Boc-Glu(Arg)-Arg (1043921-29-4)

Conditions	Yield
With 4-methyl-morpholine; sodium hydrogencarbonate In 1,4-dioxane; water pH=8.5 - 9.0;	85%

L-arginine hydrochloride (1119-34-2) + acetic anhydride (108-24-7) → N-acetyl-L-arginine (155-84-0)

Conditions	Yield
With sodium hydrogencarbonate	81%

L-arginine hydrochloride (1119-34-2) + BOC-asn-PNP (1043921-06-7) → Boc-Asp(Arg)-Arg (1043921-08-9)

Conditions	Yield
With 4-methyl-morpholine; sodium hydrogencarbonate In 1,4-dioxane; water pH=8.5 - 9.0;	80%

L-arginine hydrochloride (1119-34-2) + Allyl chloroformate (2937-50-0) → (S)-2-Allyloxycarbonylamino-5-guanidino-pentanoic acid (176230-35-6)

Conditions	Yield
With sodium hydroxide at 0℃;	79%

L-arginine hydrochloride (1119-34-2) + Z-Asn(Mbh)-ONSu (28252-61-1) → Z-Asn(Mbh)-Arg-OH (80647-49-0)

Conditions	Yield
With sodium hydroxide In water; N,N-dimethyl-formamide for 96h;	77%

diisopropyl hydrogenphosphonate (1809-20-7) + L-arginine hydrochloride (1119-34-2) → N-(diisopropylphosphoryl)arginine

Conditions	Yield
With triethylamine In tetrachloromethane; ethanol; water 1.) -15 deg C, 2 h, 2.) RT, 0.5 h;	72%

oxovanadium(IV) sulfate + 1,10-Phenanthroline (66-71-7) + L-arginine hydrochloride (1119-34-2) + salicylaldehyde (90-02-8) → [VO(N-salicylidene-L-arginine(-1H))(1,10-phenanthroline)]Cl

Conditions	Yield
With NaOH In methanol; water (N2); a mixt. of L-arginine hydrochloride and NaOH in H2O added to a MeOH soln. of salicylaldehyde, refluxed for 1 h, aq. soln. of VOSO4 added, refluxed for 30 min, C12H8N2 in MeOH added, refluxed for 30 min; concd. (vac.), filtered, washed (cold MeOH), dried (vac., P4O10), crystd. from aq. MeOH; elem. anal.;	72%

oxovanadium(IV) sulfate + L-arginine hydrochloride (1119-34-2) + salicylaldehyde (90-02-8) + dipyrazine[2,3-f:2’,3’-h]quinoxaline (217-90-3) → [VO(N-salicylidene-L-arginine(-1H))(dipyrido[3,2-d:2',3'-f]quinoxaline)]Cl

Conditions	Yield
With NaOH In methanol; water (N2); a mixt. of L-arginine hydrochloride and NaOH in H2O added to a MeOH soln. of salicylaldehyde, refluxed for 1 h, aq. soln. of VOSO4 added, refluxed for 30 min, C14H8N4 in MeOH added, refluxed for 30 min; concd. (vac.), filtered, washed (cold MeOH), dried (vac., P4O10), crystd. from aq. MeOH; elem. anal.;	68%

indolyl-3-glyoxylyl chloride (22980-09-2) + L-arginine hydrochloride (1119-34-2) + trifluoroacetic acid (76-05-1) → (+)-leptoclinidamine A trifluoroacetic acid salt

Conditions	Yield
Stage #1: indolyl-3-glyoxylyl chloride; L-arginine hydrochloride With perdeuteriopyridine In d7-N,N-dimethylformamide at 20 - 80℃; Stage #2: trifluoroacetic acid In water	67%

oxovanadium(IV) sulfate + dipyridil[3,2-a:2',3'-c]phenazine (19535-47-8) + L-arginine hydrochloride (1119-34-2) + salicylaldehyde (90-02-8) → [VO(N-salicylidene-L-arginine(-1H))(dipyrido[3,2-a:2',3'-c]phenazine)]Cl

Conditions	Yield
With NaOH In methanol; water (N2); a mixt. of L-arginine hydrochloride and NaOH in H2O added to a MeOH soln. of salicylaldehyde, refluxed for 1 h, aq. soln. of VOSO4 added, refluxed for 30 min, C18H10N4 in MeOH added, refluxed for 30 min; concd. (vac.), filtered, washed (cold MeOH), dried (vac., P4O10), crystd. from aq. MeOH; elem. anal.;	65%

ammonium cerium (IV) nitrate (16774-21-3) + Pyridine-2,6-dicarboxylic acid (499-83-2) + water (7732-18-5) + L-arginine hydrochloride (1119-34-2) → C21H9CeN3O12(2-)*C6H14N4O2*2H(1+)*7H2O

Conditions	Yield
Stage #1: ammonium cerium (IV) nitrate; Pyridine-2,6-dicarboxylic acid In methanol for 0.5h; Stage #2: water; L-arginine hydrochloride In methanol	55%

7-methoxy-3-dimethylaminomethylen-2,3-dihydro-benzo[3',2':5,6]thiopyran-4(4H)-one (1041182-97-1) + L-arginine hydrochloride (1119-34-2) → 2-(5N-ornithinyl)-8-methoxy-5H-benzo[3',2':5,6]thiopyrano[4,3-d]pyrimidine (1041183-04-3)

Conditions	Yield
Stage #1: L-arginine hydrochloride With sodium ethanolate In ethanol at 20℃; for 0.25h; Stage #2: 7-methoxy-3-dimethylaminomethylen-2,3-dihydro-benzo[3',2':5,6]thiopyran-4(4H)-one In ethanol Heating; Further stages.;	38%

L-arginine hydrochloride (1119-34-2) + trifluoroacetic acid (76-05-1) + 3,8-bis-phenoxycarbamate-ethidium dihydrophosphate → 3,8-bis-urea-arginine-ethidium tris(trifluoroacetate)

Conditions	Yield
Stage #1: L-arginine hydrochloride; 3,8-bis-phenoxycarbamate-ethidium dihydrophosphate With 2,4,6-trimethyl-pyridine In dimethyl sulfoxide at 90℃; for 1h; Stage #2: trifluoroacetic acid In water; acetonitrile	31%
Stage #1: L-arginine hydrochloride; 3,8-bis-phenoxycarbamate-ethidium dihydrophosphate With 2,4,6-trimethyl-pyridine In water; dimethyl sulfoxide at 90℃; for 1h; Stage #2: trifluoroacetic acid In water; acetonitrile	31%

copper(II) nitrate trihydrate + L-arginine hydrochloride (1119-34-2) → {Cu(L-Arg)2}(NO3)2*3H2O

Conditions	Yield
With NaOH In water soln. of Cu salt added to a soln. of the acid hydrochloride, pH adjusted to 6.5 with NaOH, standing at room temp., crystn.; collected, dried;	28%

methanol (67-56-1) + L-arginine hydrochloride (1119-34-2) → L-arginine methyl ester (2577-94-8, 65160-70-5)

Conditions	Yield
With thionyl chloride

D-Fructose (57-48-7) + L-arginine hydrochloride (1119-34-2) → α-D-Fructose-L-arginin

Conditions	Yield
In dimethyl sulfoxide

D-Fructose (57-48-7) + L-arginine hydrochloride (1119-34-2) → N-(2-deoxy-D-glucos-2-yl)-L-arginine

Conditions	Yield
In dimethyl sulfoxide

potassium cyanate (590-28-3) + L-arginine hydrochloride (1119-34-2) → Nα-carbamoyl-L-arginine (15920-89-5)

Conditions	Yield
(i) CuCO3, H2O, (ii) /BRN= 3560091/; Multistep reaction;

L-arginine hydrochloride (1119-34-2) + O-methylisourea hemisulfate (29427-58-5) → Nα-Guanyl-arginin, Nα,Nδ-Diguanyl-ornithin

Conditions	Yield
With barium dihydroxide

L-arginine hydrochloride (1119-34-2) → N-nitro-L-arginine (2149-70-4)

Conditions	Yield
With sulfuric acid; sulfur trioxide; nitric acid; Nitrogen dioxide
With ammonium nitrate; sulfuric acid

L-arginine hydrochloride (1119-34-2) + bufalin 3-hemisuberate (30219-13-7) → bufalitoxin (35455-33-5)

Conditions	Yield
With triethylamine; isobutyl chloroformate Yield given. Multistep reaction;

L-arginine hydrochloride (1119-34-2) → Citrulline (372-75-8)

Conditions	Yield
With dipotassium hydrogenphosphate; phosphoric acid; water at 25 - 37℃; Thermodynamic data; ΔH; aginine deiminase (EC 3.5.3.6) from Pseudomonas putida; var. pH and ionic strength;

L-arginine hydrochloride (1119-34-2) → dl-arginine hydrochloride (220144-84-3)

Conditions	Yield
salicylaldehyde In acetic acid at 100℃; for 1h;	100 % Turnov.

L-arginine hydrochloride (1119-34-2) → R-(-)-(1-(2)H)agmatine sulfate (83544-67-6)

Conditions	Yield
L-arginine decarboxylase In water-d2 at 36℃; for 40h;	72 mg
Multi-step reaction with 4 steps 1: 81 percent / aq. sodium bicarbonate 2: 1) deuterium oxide; 2) acetic anhydride; 3) deuterium oxide / 2) perdeuterio acetic acid, reflux, 2 h; 3) reflux, 30 min 3: hog kidney acylase I 4: 100 mg / 40 h / 36 °C / enzymic decarboxylation with L-arginine decarboxylase View Scheme
Multi-step reaction with 4 steps 1: 81 percent / aq. sodium bicarbonate 2: 1) deuterium oxide; 2) acetic anhydride; 3) deuterium oxide / 2) perdeuterio acetic acid, reflux, 2 h; 3) reflux, 30 min 4: 100 mg / 40 h / 36 °C / enzymic decarboxylation with L-arginine decarboxylase View Scheme

L-arginine hydrochloride (1119-34-2) → R-(-)-(1-(2)H)agmatine sulfate (83544-65-4)

Conditions	Yield
With d(3)-acetic acid; sulfuric acid; water-d2; sodium carbonate 2) deuterium oxide, enzymic decarboxylation with L-arginine decarboxylase, 36 deg C, 30-40 h; 2) water; Yield given. Multistep reaction;

L-arginine hydrochloride (1119-34-2) → L-ornithine hydrochloride (3184-13-2) + urea (57-13-6)

Conditions	Yield
With dipotassium hydrogenphosphate; phosphoric acid; water at 25 - 37.1℃; Thermodynamic data; ΔH; arginase (EC 3.5.3.1); var. pH and ionic strength;

L-arginine hydrochloride (1119-34-2) + 4-Isobutoxycarbonyloxy-4-oxo-butyric acid (3S,8R,9S,10R,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(6-oxo-6H-pyran-3-yl)-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester (1058650-87-5) → scillarenin 3-succinyl-L-arginine ester

Conditions	Yield
In tetrahydrofuran; methanol at 0℃; for 2h; Yield given;

Upstream product

• 1207348-80-8 micropeptin MZ₇₇₁ 
• 1207348-78-4 micropeptin MZ₁₀₁₉ 
• 1207348-76-2 micropeptin MZ₉₃₉B 
• 1207348-74-0 micropeptin MZ₉₂₅ 
• 1207348-72-8 micropeptin MZ₉₃₉A 
• 1207348-70-6 micropeptin MZ₈₅₉ 
• 914606-75-0 micropeptin MZ₈₄₅ 
• 74-79-3 L-arginine 

Downstream Products

• 70-26-8 2,5-diaminopentanoic acid 
• 113-00-8 guanidine nitrate 
• 128424-99-7 C₁₅H₂₂N₈O₇ 
• 2577-94-8 L-arginine methyl ester 
• 33171-13-0 L‐arginine ethyl ester hydrochloride 
• 33171-13-0 arginine ethyl ester hydrochloride 
• 17907-22-1 ^αN,^ωN-bis(tertbutoxycarbonyl)-L-arginine 
• 13726-76-6 t-butyloxycarbonyl-L-arginine 
• 22888-59-1 L-arginine methyl ester dihydrochloride 
• 23734-44-3 Cbo-L-Val-nitro-L-Arg-methylester 
• 106386-18-9 α-Carbobenzoxy-ω-nitro-L-arginyl-ω-carbobenzoxy-L-lysin-methylester 
• 23814-96-2 (Z)-Arg(NO₂)-Arg(NO₂)-OMe 

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Ruckerbactin Produced by Yersinia ruckeri YRB Is a Diastereomer of the Siderophore Trivanchrobactin Produced by Vibrio campbellii DS40M4

The Gram-negative bacterium Yersinia ruckeri is the causative agent for enteric red mouth disease in salmonids. The genome of Y. ruckeri YRB contains a biosynthetic gene cluster encoding the biosynthesis of catechol siderophores that are diastereomeric with the known vanchrobactin class of siderophores, (DHBDArgLSer)(1–3). Ruckerbactin (1), produced by Y. ruckeri YRB, was found to be the linear tris-l-serine ester composed of l-arginine and 2,3-dihydroxybenzoic acid, (DHBLArgLSer)3. The biscatechol, (DHBLArgLSer)2 (2), and monocatechol, DHBLArgLSer (3), compounds were also isolated and characterized. The macrolactone of ruckerbactin was not detected. The presence of LArg in ruckerbactin makes it the diastereomer of trivanchrobactin with DArg. The electronic circular dichroism spectra of Fe(III)–ruckerbactin and Fe(III)–trivanchrobactin reveal the opposite enantiomeric configurations at the Fe(III) sites. Fe(III)–ruckerbactin adopts the Δ configuration, and Fe(III)–trivanchrobactin adopts the Λ configuration. Y. ruckeri YRB was also found to produce the antimicrobial agent holomycin (4).

LAT1 activity of carboxylic acid bioisosteres: Evaluation of hydroxamic acids as substrates

Large neutral amino acid transporter 1 (LAT1) is a solute carrier protein located primarily in the blood–brain barrier (BBB) that offers the potential to deliver drugs to the brain. It is also up-regulated in cancer cells, as part of a tumor's increased metabolic demands. Previously, amino acid prodrugs have been shown to be transported by LAT1. Carboxylic acid bioisosteres may afford prodrugs with an altered physicochemical and pharmacokinetic profile than those derived from natural amino acids, allowing for higher brain or tumor levels of drug and/or lower toxicity. The effect of replacing phenylalanine's carboxylic acid with a tetrazole, acylsulfonamide and hydroxamic acid (HA) bioisostere was examined. Compounds were tested for their ability to be LAT1 substrates using both cis-inhibition and trans-stimulation cell assays. As HA-Phe demonstrated weak substrate activity, its structure–activity relationship (SAR) was further explored by synthesis and testing of HA derivatives of other LAT1 amino acid substrates (i.e., Tyr, Leu, Ile, and Met). The potential for a false positive in the trans-stimulation assay caused by parent amino acid was evaluated by conducting compound stability experiments for both HA-Leu and the corresponding methyl ester derivative. We concluded that HA's are transported by LAT1. In addition, our results lend support to a recent account that amino acid esters are LAT1 substrates, and that hydrogen bonding may be as important as charge for interaction with the transporter binding site.

Polyunsaturated fatty acid derivatives, pharmaceutical compositions containing the same, method for the preparation thereof, and their use as medicament

The compounds of the Formula (I) STR1 wherein R1 is a C18-24 alkenyl containing at least two double bonds, or --(CH2)n --CH(NH2)m --COOH X is 0, NH or C1-4 alkyl-N, Y is CONH2, COOH or COOMe, wherein Me is hydrogen metal, and R2 is a side chain of a any amino acid except L-GLU or L-ASP at α-position or a group of Formula wherein k is zero or an integer of 1, n is zero or an integer of 1 to 3, m is zero or an integer of 1 to 4, A is hydroxyl or one A is hydroxyl and the other A is hydrogen. M is H or R1 --CO and X and R1 are as defined above and their salts having tyrosine kinase inhibitor activity can be used as antitumor agents.