25546-65-0

Usage

Uses

Used in Pharmaceutical Industry:
RIBOSTAMYCIN SULFATE SALT is used as an antibiotic for treating various bacterial infections. Its application is primarily due to its ability to inhibit bacterial protein synthesis by targeting the ribosome, thus disrupting the growth and replication of the bacteria.
Used in Research and Development:
In the field of research and development, RIBOSTAMYCIN SULFATE SALT is utilized as a valuable tool for studying the mechanisms of bacterial protein synthesis and antibiotic resistance. This understanding can lead to the development of new antibiotics and strategies to combat drug-resistant bacteria.
Used in Veterinary Medicine:
RIBOSTAMYCIN SULFATE SALT is also employed in veterinary medicine as an antibiotic to treat bacterial infections in animals. Its use helps maintain the health of livestock and pets, ensuring the well-being of both the animals and their human caretakers.
Used in Drug Resistance Studies:
RIBOSTAMYCIN SULFATE SALT serves as a crucial compound in studying the development of antibiotic resistance in bacteria. By examining the interactions between this antibiotic and bacterial strains, researchers can gain insights into the evolution of resistance mechanisms and develop strategies to counteract them.

InChI:InChI=1/C17H34N4O10/c18-2-6-10(24)12(26)8(21)16(28-6)30-14-5(20)1-4(19)9(23)15(14)31-17-13(27)11(25)7(3-22)29-17/h4-17,22-27H,1-3,18-21H2/t4-,5+,6-,7-,8-,9?,10-,11-,12-,13-,14-,15-,16-,17+/m1/s1

Synthetic route

tetra-N-acetylribostamycin (28440-41-7, 64999-27-5, 64999-28-6) → ribostamycin (25546-65-0)

Conditions	Yield
With hydrazine hydrate at 100℃; for 66h; sealed tube;	59%

1,3,2',6'-Tetra-N-(benzyloxycarbonyl)-2'',3'',5''-tri-O-benzoyl-6,3',4'-tri-O-benzylribostamycin (78763-89-0) → ribostamycin (25546-65-0)

Conditions	Yield
With palladium on activated charcoal; hydrogen; sodium methylate; acetic acid 1.) MeOH, 3.5 h, 2.) aq. dioxane, 48 h, then water; Yield given. Multistep reaction;

[(1S,2R,3R,5R)-2-[(2R,3R,4R,5S,6R)-3-Acetylamino-6-(acetylamino-methyl)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-3-((2S,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yloxy)-4,6-dihydroxy-5-nitro-cyclohexyl]-carbamic acid benzyl ester (96181-96-3) → ribostamycin (25546-65-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) p-TsOH*H2O; 2.) pyridine; 3.) d-10-camphorsulfonic acid / 1.) DMF, 45 deg C, 50 min; 2.) r.t., 8 h; 3.) DMF, r.t., 10 min 3: 59 percent / 80percent aq. NH2NH2*H2O / 66 h / 100 °C / sealed tube View Scheme

C41H53N3O23 (96181-94-1) → ribostamycin (25546-65-0)

Conditions	Yield
Multi-step reaction with 5 steps 1: benzene; pyridine / 1 h / Heating 2: 62 percent / NaOMe / methanol; nitromethane / 14 h / Ambient temperature 3: 1.) p-TsOH*H2O; 2.) pyridine; 3.) d-10-camphorsulfonic acid / 1.) DMF, 45 deg C, 50 min; 2.) r.t., 8 h; 3.) DMF, r.t., 10 min 5: 59 percent / 80percent aq. NH2NH2*H2O / 66 h / 100 °C / sealed tube View Scheme

C55H66N4O18 (96200-99-6) → ribostamycin (25546-65-0)

Conditions	Yield
Multi-step reaction with 2 steps 2: 59 percent / 80percent aq. NH2NH2*H2O / 66 h / 100 °C / sealed tube View Scheme

C59H69N3O22 (96181-92-9) → ribostamycin (25546-65-0)

Conditions

Yield

Multi-step reaction with 7 steps 1: pyridine 2: 1.) BF3-Et2O; 2.) Jones reagent / 1.) THF, 2 deg C, 40 min; 2.) r.t., 4 h 3: benzene; pyridine / 1 h / Heating 4: 62 percent / NaOMe / methanol; nitromethane / 14 h / Ambient temperature 5: 1.) p-TsOH*H2O; 2.) pyridine; 3.) d-10-camphorsulfonic acid / 1.) DMF, 45 deg C, 50 min; 2.) r.t., 8 h; 3.) DMF, r.t., 10 min 7: 59 percent / 80percent aq. NH2NH2*H2O / 66 h / 100 °C / sealed tube View Scheme

C61H71N3O23 (96181-93-0) → ribostamycin (25546-65-0)

Conditions

Yield

Multi-step reaction with 6 steps 1: 1.) BF3-Et2O; 2.) Jones reagent / 1.) THF, 2 deg C, 40 min; 2.) r.t., 4 h 2: benzene; pyridine / 1 h / Heating 3: 62 percent / NaOMe / methanol; nitromethane / 14 h / Ambient temperature 4: 1.) p-TsOH*H2O; 2.) pyridine; 3.) d-10-camphorsulfonic acid / 1.) DMF, 45 deg C, 50 min; 2.) r.t., 8 h; 3.) DMF, r.t., 10 min 6: 59 percent / 80percent aq. NH2NH2*H2O / 66 h / 100 °C / sealed tube View Scheme

C43H57N3O23 (96181-90-7) → ribostamycin (25546-65-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: 62 percent / NaOMe / methanol; nitromethane / 14 h / Ambient temperature 2: 1.) p-TsOH*H2O; 2.) pyridine; 3.) d-10-camphorsulfonic acid / 1.) DMF, 45 deg C, 50 min; 2.) r.t., 8 h; 3.) DMF, r.t., 10 min 4: 59 percent / 80percent aq. NH2NH2*H2O / 66 h / 100 °C / sealed tube View Scheme

ribostamycin (25546-65-0) + γ-L-Glu-((S)-4-amino-2-hydroxybutyryl)-N-acetylcysteamine thioester (1064665-41-3) → γ-L-Glu-butirosin B (1064665-42-4)

Conditions	Yield
With recombinant BtrH enzyme at 20℃; for 6h; pH=7.9; aq. buffer; Enzymatic reaction;	100%

ribostamycin (25546-65-0) + trityl chloride (76-83-5) → 1,3,2',6'-tetra-N-trityl-5''-mono-O-trityl-ribostamycin

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 50℃; for 72h;	70%

ribostamycin (25546-65-0) + heptafluorobutyric Acid (375-22-4) → C-3-azidoribostamycin tri(heptafluorobutyric acid)

Conditions	Yield
Stage #1: ribostamycin With 1H-imidazole-1-sulfonyl azide hydrochloride; sodium hydroxide In aq. phosphate buffer at 20℃; for 18h; pH=8; Stage #2: heptafluorobutyric Acid In acetone at 40℃; regioselective reaction;	44%

ribostamycin (25546-65-0) + ATP (56-65-5) → C27H46N9O16P

Conditions	Yield
at 37℃; aminoglycoside-4'-nucleotidyltransferaze of Bacillus brevis, MgCl2, potassium phosphate buffer (pH 6.0);

ribostamycin (25546-65-0) + N-tertiarybutoxycarbonyl-β-alanine N-hydroxysuccinimide ester (32703-87-0) → [2-({(2R,3S,4R,5R,6R)-5-Amino-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-((2S,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yloxy)-3-hydroxy-cyclohexyloxy]-3,4-dihydroxy-tetrahydro-pyran-2-ylmethyl}-carbamoyl)-ethyl]-carbamic acid tert-butyl ester (693776-12-4)

endo-N-hydroxy-5-norbornene-2,3-dicarboximide O-bromoacetate (872054-82-5) + ribostamycin (25546-65-0) → N-{(2R,3S,4R,5R,6R)-5-Amino-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-((2S,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yloxy)-3-hydroxy-cyclohexyloxy]-3,4-dihydroxy-tetrahydro-pyran-2-ylmethyl}-2-bromo-acetamide

Conditions	Yield
In water; acetonitrile at 20℃; for 0.166667h;
In water; acetonitrile for 0.166667h; Product distribution / selectivity;

ribostamycin (25546-65-0) → 6'-N-β-alanine-1,3,3'-N-guanidinoribostamycin

Conditions	Yield
Multi-step reaction with 3 steps 1: Et3N 2: trifluoroacetic acid / CH2Cl2 View Scheme

ribostamycin (25546-65-0) → C58H101N11O25 (693776-13-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N View Scheme

ribostamycin (25546-65-0) + YALPETGK (950832-64-1) → C49H80N10O20 (950832-57-2)

Conditions	Yield
With Tris-HCl buffer; 2-hydroxyethanethiol; transpeptidase sortase A from Staphylococcus aureus at 37℃; for 6h; pH=7.5; Enzymatic reaction;	21.7 % Chromat.

ribostamycin (25546-65-0) + YALPMTGK (950832-65-2) → C49H82N10O18S (950832-47-0)

Conditions	Yield
With Tris-HCl buffer; 2-hydroxyethanethiol; transpeptidase sortase A from Staphylococcus aureus at 37℃; for 6h; pH=7.5; Enzymatic reaction;	22.1 % Chromat.

ribostamycin (25546-65-0) + acetylcoenzyme A (72-89-9) → 2'-N-acetyl-ribostamycin

Conditions	Yield
With MES buffer at 20℃; for 16h; pH=6;

ribostamycin (25546-65-0) + P'-[2-(acetylamino)-2-deoxy-α-D-glucopyranosyl] ester uridine 5'-(trihydrogen diphosphate), disodium salt (91183-98-1) → N-acetylglucosaminylribostamycin (1079925-74-8)

Conditions	Yield
With Neo 15 protein expressed with an N-terminal His6-tag in Escherichia coli BL21 (DE3), the mass = 41295 Da (including the His6-tag and with loss of N-terminal methionine), glycosyltransferase at 30℃; pH=8.4; aq. buffer; Enzymatic reaction;

ribostamycin (25546-65-0) → 5'-O-(4,4'-dimethoxytrityl)-1,3,2',6'-tetra-N-trifluoroacetylribostamycin (1315508-28-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / methanol / 20 °C 2: pyridine View Scheme

ribostamycin (25546-65-0) + trifluoroacetic acid-methyl ester (431-47-0) → C25H30F12N4O14 (1315508-27-0)

Conditions	Yield
With triethylamine In methanol at 20℃;

Upstream product

• 28440-41-7 tetra-N-acetylribostamycin 
• 78763-89-0 1,3,2',6'-Tetra-N-(benzyloxycarbonyl)-2'',3'',5''-tri-O-benzoyl-6,3',4'-tri-O-benzylribostamycin 
• 96181-90-7 C₄₃H₅₇N₃O₂₃ 
• 96181-93-0 C₆₁H₇₁N₃O₂₃ 
• 96181-92-9 C₅₉H₆₉N₃O₂₂ 
• 96200-99-6 C₅₅H₆₆N₄O₁₈ 
• 96181-94-1 C₄₁H₅₃N₃O₂₃ 
• 96181-96-3 [(1S,2R,3R,5R)-2-[(2R,3R,4R,5S,6R)-3-Acetylamino-6-(acetylamino-methyl)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-3-((2S,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yloxy)-4,6-dihydroxy-5-nitro-cyclohexyl]-carbamic acid benzyl ester 

Downstream Products

• 693776-12-4 [2-({(2R,3S,4R,5R,6R)-5-Amino-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-((2S,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yloxy)-3-hydroxy-cyclohexyloxy]-3,4-dihydroxy-tetrahydro-pyran-2-ylmethyl}-carbamoyl)-ethyl]-carbamic acid tert-butyl ester 
• 950832-57-2 C₄₉H₈₀N₁₀O₂₀ 
• 1315508-27-0 C₂₅H₃₀F₁₂N₄O₁₄ 
• 1315508-28-1 5'-O-(4,4'-dimethoxytrityl)-1,3,2',6'-tetra-N-trifluoroacetylribostamycin 
• 1079925-74-8 N-acetylglucosaminylribostamycin 
• 1064665-42-4 γ-L-Glu-butirosin B 
• 693776-13-5 C₅₈H₁₀₁N₁₁O₂₅ 

Relevant academic research and scientific papers

SYNTHESIS OF RIBOSTAMYCIN. AN APPLICATION OF A CHEMICAL CONVERSION METHOD FROM CARBOHYDRATE TO AMINOCYCLITOL

An aminoglycoside antibiotic ribostamycin was synthesized from D-glucosamine and ribose via an amino-trisaccharide intermediate, which was prepared through successive selective glycosidations on the 1,6-anhydro-D-glucosamine moiety.