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58-85-5 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 58-85-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 8 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 58-85:
(4*5)+(3*8)+(2*8)+(1*5)=65
65 % 10 = 5
So 58-85-5 is a valid CAS Registry Number.
InChI:InChI=1/C10H16N2O3S/c13-8(14)4-2-1-3-7-9-6(5-16-7)11-10(15)12-9/h6-7,9H,1-5H2,(H,13,14)(H2,11,12,15)/p-1/t6-,7-,9+/m0/s1

58-85-5 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Detail
  • TCI America

  • (B0463)  Biotin  >98.0%(T)

  • 58-85-5

  • 100mg

  • 80.00CNY

  • Detail
  • TCI America

  • (B0463)  Biotin  >98.0%(T)

  • 58-85-5

  • 1g

  • 299.00CNY

  • Detail
  • TCI America

  • (B0463)  Biotin  >98.0%(T)

  • 58-85-5

  • 5g

  • 980.00CNY

  • Detail
  • Alfa Aesar

  • (A14207)  D-(+)-Biotin, 98+%   

  • 58-85-5

  • 1g

  • 547.0CNY

  • Detail
  • Alfa Aesar

  • (A14207)  D-(+)-Biotin, 98+%   

  • 58-85-5

  • 5g

  • 2390.0CNY

  • Detail
  • Alfa Aesar

  • (A14207)  D-(+)-Biotin, 98+%   

  • 58-85-5

  • 10g

  • 3945.0CNY

  • Detail
  • Alfa Aesar

  • (A14207)  D-(+)-Biotin, 98+%   

  • 58-85-5

  • 25g

  • 8547.0CNY

  • Detail
  • Sigma-Aldrich

  • (91827)  Biotin  certified reference material, TraceCERT®

  • 58-85-5

  • 91827-50MG

  • 1,055.34CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1233)  Biotin  pharmaceutical secondary standard; traceable to USP and PhEur

  • 58-85-5

  • PHR1233-1G

  • 952.15CNY

  • Detail
  • Sigma-Aldrich

  • (B1116000)  Biotin  European Pharmacopoeia (EP) Reference Standard

  • 58-85-5

  • B1116000

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (19606)  Biotin  tested according to Ph.Eur.

  • 58-85-5

  • 19606-1G-F

  • 3,536.91CNY

  • Detail
  • USP

  • (1071508)  Biotin  United States Pharmacopeia (USP) Reference Standard

  • 58-85-5

  • 1071508-200MG

  • 4,662.45CNY

  • Detail

58-85-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name biotin

1.2 Other means of identification

Product number -
Other names FACTOR S

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:58-85-5 SDS

58-85-5Synthetic route

(2S,3S,4S)-5-(3,4-diaminotetrahydrothiophen-2-yl)pentanoic acid

(2S,3S,4S)-5-(3,4-diaminotetrahydrothiophen-2-yl)pentanoic acid

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

biotin
58-85-5

biotin

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; tin(IV) chloride at 150℃; under 300.03 Torr; for 3.5h; Temperature; Pressure; Reagent/catalyst; Autoclave;97.5%
(3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione
28092-52-6

(3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione

potassium thioacetate
10387-40-3

potassium thioacetate

biotin
58-85-5

biotin

Conditions
ConditionsYield
In water at 0 - 60℃; Temperature;97%
5-((3aR,6S,6aS)-1-Benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic acid

5-((3aR,6S,6aS)-1-Benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic acid

biotin
58-85-5

biotin

Conditions
ConditionsYield
With hydrogenchloride; sodium dithionite; water; sodium hydroxide In water at 55 - 90℃; for 0.5h; Reagent/catalyst;95.8%
(3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene)pentanoic acid
33607-60-2

(3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene)pentanoic acid

biotin
58-85-5

biotin

Conditions
ConditionsYield
Stage #1: (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene)pentanoic acid With boron tribromide In dichloromethane at -5 - 50℃; for 1.16667h; Inert atmosphere;
Stage #2: With hydrogenchloride In water Temperature; Solvent;
95%
Stage #1: (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene)pentanoic acid With water; hydrogen bromide In xylene for 20h; Heating / reflux;
Stage #2: With sodium hydroxide In water pH=12;
Stage #3: With hydrogenchloride; bis(trichloromethyl) carbonate; pyrographite Product distribution / selectivity; more than 3 stages;
92%
Stage #1: (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene)pentanoic acid With water; hydrogen bromide In xylene for 20h; Heating / reflux;
Stage #2: With sodium hydroxide In water pH=12;
Stage #3: With hydrogenchloride; bis(trichloromethyl) carbonate; pyrographite Product distribution / selectivity; more than 3 stages;
92%
(3aS,4S,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2(3H)-one-4-ylpentane nitrile
31099-31-7

(3aS,4S,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2(3H)-one-4-ylpentane nitrile

biotin
58-85-5

biotin

Conditions
ConditionsYield
Stage #1: (3aS,4S,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2(3H)-one-4-ylpentane nitrile With water; hydrogen bromide In xylene for 20h; Heating / reflux;
Stage #2: With sodium hydroxide In water pH=12;
Stage #3: With hydrogenchloride; bis(trichloromethyl) carbonate; pyrographite Product distribution / selectivity; more than 3 stages;
95%
With water; hydrogen bromide for 10h; Reflux; Inert atmosphere;80%
Multi-step reaction with 2 steps
1: aq. HBr / toluene / 40 h / Heating
2: 22 g / aq. NaOH / toluene; methoxybenzene / 6 h / 30 °C
View Scheme
5-[(2S,3S,4R)-3,4-diaminotetrahydrothiophen-2-yl]pentanoic acid hydrobromide

5-[(2S,3S,4R)-3,4-diaminotetrahydrothiophen-2-yl]pentanoic acid hydrobromide

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

biotin
58-85-5

biotin

Conditions
ConditionsYield
With sodium hydroxide at 20℃; for 10h; pH=9-11;93%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

5-[(2S,3S,4R)-3,4-diaminotetrahydrothiophen-2-yl]pentanoic acid hydrobromide

5-[(2S,3S,4R)-3,4-diaminotetrahydrothiophen-2-yl]pentanoic acid hydrobromide

biotin
58-85-5

biotin

Conditions
ConditionsYield
With potassium hydroxide at 20℃; for 10h; pH=9-11; Reagent/catalyst;92%
(2S,3S,4S)-5-(3,4-diaminotetrahydrothiophen-2-yl)pentanoic acid

(2S,3S,4S)-5-(3,4-diaminotetrahydrothiophen-2-yl)pentanoic acid

Diethyl carbonate
105-58-8

Diethyl carbonate

biotin
58-85-5

biotin

Conditions
ConditionsYield
With methanetrisulfonic acid at 170℃; under 3000.3 - 4500.45 Torr; Reagent/catalyst; Pressure; Temperature; Autoclave;91.67%
(3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene)pentanoic acid ethyl ester
292151-19-0

(3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene)pentanoic acid ethyl ester

biotin
58-85-5

biotin

Conditions
ConditionsYield
Stage #1: (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene)pentanoic acid ethyl ester With water; hydrogen bromide In xylene for 20h; Heating / reflux;
Stage #2: With sodium hydroxide In water pH=12;
Stage #3: With hydrogenchloride; bis(trichloromethyl) carbonate; pyrographite Product distribution / selectivity; more than 3 stages;
90%
With sulfuric acid; water; acetic acid at 20 - 80℃;82%
With methanesulfonic acid In 1,3,5-trimethyl-benzene74%
Stage #1: (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene)pentanoic acid ethyl ester With hydrogen bromide for 48h; Substitution; Heating;
Stage #2: With sodium hydroxide; chloroformic acid ethyl ester Substitution;
Stage #3: With hydrogenchloride Hydrolysis;
benzyl (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl)pentanoate
179532-60-6

benzyl (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl)pentanoate

biotin
58-85-5

biotin

Conditions
ConditionsYield
Stage #1: benzyl (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl)pentanoate With water; hydrogen bromide In xylene for 24h; Heating / reflux;
Stage #2: With sodium hydroxide In water pH=12;
Stage #3: With hydrogenchloride; trichloromethyl chloroformate; pyrographite Product distribution / selectivity; more than 3 stages;
90%
Stage #1: benzyl (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl)pentanoate With water; hydrogen bromide In xylene for 20h; Heating / reflux;
Stage #2: With sodium hydroxide In water pH=12;
Stage #3: With hydrogenchloride; trichloromethyl chloroformate; pyrographite Product distribution / selectivity; more than 3 stages;
90%
C19H24N2O3S

C19H24N2O3S

biotin
58-85-5

biotin

Conditions
ConditionsYield
Stage #1: C19H24N2O3S With palladium on activated charcoal; hydrogen In ethanol at 80 - 85℃; under 11400.8 - 15201 Torr; for 15h;
Stage #2: With sodium hydroxide In water at 25 - 30℃; for 5h; Solvent;
86.9%
<3aS-(3aα,4β,6aα)>-Hexahydro-2-oxo-3-(phenylmethyl)-1H-thieno<3,4-d>imidazole-4-pentanoic acid methyl ester
83541-80-4

<3aS-(3aα,4β,6aα)>-Hexahydro-2-oxo-3-(phenylmethyl)-1H-thieno<3,4-d>imidazole-4-pentanoic acid methyl ester

biotin
58-85-5

biotin

Conditions
ConditionsYield
With hydrogen bromide85%
With hydrogen bromide85%
<3aS-(3aα,4β,6aα)>-Hexahydro-2-oxo-1-(phenylmethyl)-1H-thieno<3,4-d>imidazole-4-pentanoic acid methyl ester
151526-81-7

<3aS-(3aα,4β,6aα)>-Hexahydro-2-oxo-1-(phenylmethyl)-1H-thieno<3,4-d>imidazole-4-pentanoic acid methyl ester

biotin
58-85-5

biotin

Conditions
ConditionsYield
With hydrogen bromide for 2h; Heating;85%
With hydrogen bromide for 2h; Heating;85%
Multi-step reaction with 2 steps
1.1: water; NaOH / methanol / 3 h / 40 °C
2.1: MeSO3H / xylene / 3 h / 135 °C
2.2: 3.06 g / water / 1 h / 10 °C
View Scheme
(3aS,6aR)-1,3-Dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2(3H)-one-4-ylidenepentanoic acid
324012-42-2

(3aS,6aR)-1,3-Dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2(3H)-one-4-ylidenepentanoic acid

biotin
58-85-5

biotin

Conditions
ConditionsYield
With formic acid; methanesulfonic acid; palladium on activated charcoal for 15h; Catalytic hydrogenation; Debenzylation; Heating;85%
Multi-step reaction with 2 steps
1: H2 / 10percent Pd/C / propan-2-ol / 18 h / 50 °C / 7500.6 Torr
2: 48percent HBr / 2 h / 100 °C
View Scheme
ethyl 5-iodopentanoate

ethyl 5-iodopentanoate

(3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione
28092-52-6

(3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione

biotin
58-85-5

biotin

Conditions
ConditionsYield
Stage #1: ethyl 5-iodopentanoate With bromine; zinc In tetrahydrofuran; toluene at 40℃; for 1h;
Stage #2: (3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione With palladium 10% on activated carbon In tetrahydrofuran; N,N-dimethyl-formamide; toluene at 28 - 40℃; for 5h; Further stages;
85%
(1-naphthyl)CH2CONH(CH2)2OPO2O-5\-d(GCGAGAAGTTAAGACCTATGCTCGC)-3\-O(CH2)3S-(4-succinimide-1)-(CH2)2O-(p-C6H4)COCH2(biotinate)

(1-naphthyl)CH2CONH(CH2)2OPO2O-5\-d(GCGAGAAGTTAAGACCTATGCTCGC)-3\-O(CH2)3S-(4-succinimide-1)-(CH2)2O-(p-C6H4)COCH2(biotinate)

biotin
58-85-5

biotin

Conditions
ConditionsYield
With 5'-d(CATAGGTCTTAACTT)-3'; sodium cacodylate In water; isopropyl alcohol at 20℃; pH=7.0; UV-irradiation;84%
N,N'-p-methoxybenzylbiotin
1245507-48-5

N,N'-p-methoxybenzylbiotin

biotin
58-85-5

biotin

Conditions
ConditionsYield
Stage #1: N,N'-p-methoxybenzylbiotin With hydrogen bromide In toluene for 36h; Reflux;
Stage #2: With bis(trichloromethyl) carbonate; methoxybenzene In water for 2h; pH=10;
83%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

(2S,3S,4S)-5-(3,4-diaminotetrahydrothiophen-2-yl)pentanoic acid

(2S,3S,4S)-5-(3,4-diaminotetrahydrothiophen-2-yl)pentanoic acid

biotin
58-85-5

biotin

Conditions
ConditionsYield
With sodium hydroxide In water; toluene at -10 - -5℃;82.38%
biotin
58-85-5

biotin

Conditions
ConditionsYield
Stage #1: N,N'-dibenzylbiotin methyl ester With hydrogen bromide for 5h; Heating;
Stage #2: With sulfuric acid In methanol for 2h; Heating;
78%
With hydrogen bromide for 5h; Heating;0.041 g
phosgene
75-44-5

phosgene

(2S,3S,4R-3,4-diaminotetrahydrothiophen-2-yl)-pentanoate sodium

(2S,3S,4R-3,4-diaminotetrahydrothiophen-2-yl)-pentanoate sodium

biotin
58-85-5

biotin

Conditions
ConditionsYield
With sodium hydroxide In water; 1,2-dichloro-ethane at 70 - 80℃; for 4h; pH=10 - 12;75.8%
hept-6-ynoic acid
30964-00-2

hept-6-ynoic acid

amine-biotin

amine-biotin

isobutyl chloroformate
543-27-1

isobutyl chloroformate

A

alk-biotin

alk-biotin

B

biotin
58-85-5

biotin

Conditions
ConditionsYield
With 4-methyl-morpholine In dichloromethane; N,N-dimethyl-formamideA n/a
B 62%
phosgene
75-44-5

phosgene

(2S,3S,4R)-cis-5-(3,4-diaminotetrahydro-2-thienyl)valeric acid
22342-46-7

(2S,3S,4R)-cis-5-(3,4-diaminotetrahydro-2-thienyl)valeric acid

biotin
58-85-5

biotin

Conditions
ConditionsYield
With MANDELIC ACID
With (9S)-9-hydroxy-6'-methoxy-1-methyl-cinchonanium hydroxide
With L-arginine
5-[(3aS)-1( oder !3)-benzyl-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl]-valeric acid
76335-62-1

5-[(3aS)-1( oder !3)-benzyl-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl]-valeric acid

biotin
58-85-5

biotin

Conditions
ConditionsYield
With ammonia; sodium; xylene
Stage #1: 5-[(3aS)-1( oder !3)-benzyl-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl]-valeric acid With methanesulfonic acid In xylene at 135℃; for 3h;
Stage #2: With water at 10℃; for 1h; Further stages.;
3.06 g
With ammonia; sodium; xylene
phosgene
75-44-5

phosgene

5-[3,4-bis-(2,2,2-trifluoro-acetylamino)-2,5-dihydro-thiophen-2-yl]-pentanoic acid methyl ester
64820-06-0

5-[3,4-bis-(2,2,2-trifluoro-acetylamino)-2,5-dihydro-thiophen-2-yl]-pentanoic acid methyl ester

biotin
58-85-5

biotin

Conditions
ConditionsYield
(i) H2, Pd/C, (ii) K2CO3, H2O, (iii) /BRN= 1098367/; Multistep reaction;
[3-((3aS)-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl)-propyl]-malonic acid
57671-79-1

[3-((3aS)-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl)-propyl]-malonic acid

biotin
58-85-5

biotin

Conditions
ConditionsYield
With sodium hydroxide at 180℃; for 0.5h;
5-((3aS)-1,3-diacetyl-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl)-pentanoic acid methyl ester
66244-06-2

5-((3aS)-1,3-diacetyl-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl)-pentanoic acid methyl ester

biotin
58-85-5

biotin

Conditions
ConditionsYield
With sodium hydroxide In methanol; water
Sodium; 5-((3aR,6S,6aS)-1-benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoate

Sodium; 5-((3aR,6S,6aS)-1-benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoate

biotin
58-85-5

biotin

Conditions
ConditionsYield
With hydrogen bromide for 2h; Heating;
methanol
67-56-1

methanol

biotin
58-85-5

biotin

biotin methyl ester

biotin methyl ester

Conditions
ConditionsYield
With hydrogenchloride for 15h;100%
With sulfuric acid100%
Stage #1: methanol With acetyl chloride at 0℃; for 0.166667h;
Stage #2: biotin for 1h; Reflux;
100%
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

biotin
58-85-5

biotin

biotin N-Hydroxysuccinimide ester
35013-72-0

biotin N-Hydroxysuccinimide ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃;100%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Inert atmosphere;98%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;95%
ethanol
64-17-5

ethanol

biotin
58-85-5

biotin

5-[(3aS,4S,6aR)-2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl]-pentanoic acid ethyl ester
87573-52-2

5-[(3aS,4S,6aR)-2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl]-pentanoic acid ethyl ester

Conditions
ConditionsYield
With sulfuric acid100%
With sulfuric acid at 20℃;97%
With hydrogenchloride at 0 - 20℃; for 24h;91%
methyl 10-aminodecanoate hydrochloride
106590-42-5

methyl 10-aminodecanoate hydrochloride

biotin
58-85-5

biotin

10-[5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-decanoic acid methyl ester

10-[5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-decanoic acid methyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide100%
glycine ethyl ester hydrochloride
5680-79-5

glycine ethyl ester hydrochloride

biotin
58-85-5

biotin

[5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-acetic acid methyl ester

[5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-acetic acid methyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide100%
tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate
153086-78-3

tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate

biotin
58-85-5

biotin

tert-butyl-N-(2-(2-(2-(5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno(3,4-d)imidazol-6-yl)pentanoylamino)ethoxy)ethoxy)ethyl)carbamate
175885-18-4

tert-butyl-N-(2-(2-(2-(5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno(3,4-d)imidazol-6-yl)pentanoylamino)ethoxy)ethoxy)ethyl)carbamate

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h;100%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 17.5h; Inert atmosphere;100%
Stage #1: biotin With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate In dichloromethane at 20℃; for 16h;
96%
C2HF3O2*C6H14N4O2
929537-66-6

C2HF3O2*C6H14N4O2

biotin
58-85-5

biotin

N-(2-(2-(2-azidoethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide
945633-30-7

N-(2-(2-(2-azidoethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide

Conditions
ConditionsYield
With 2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetratetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide100%
C8H17NO5

C8H17NO5

biotin
58-85-5

biotin

C19H33N3O7S
1123762-87-7

C19H33N3O7S

Conditions
ConditionsYield
With 2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetratetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide100%
1-(benzylthio)-3-(tert-butyldiphenylsilyloxy)propan-2-amine
1278996-71-6

1-(benzylthio)-3-(tert-butyldiphenylsilyloxy)propan-2-amine

biotin
58-85-5

biotin

1-(benzylthio)-3-(tert-butyldiphenylsilyloxy)propan-2-biotinylamide
1278996-72-7

1-(benzylthio)-3-(tert-butyldiphenylsilyloxy)propan-2-biotinylamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 24h;100%
N,N-dimethylethylenediamine

N,N-dimethylethylenediamine

biotin
58-85-5

biotin

2-N-biotinyl-N,N-dimethylethan-1,2-diamine
1338832-53-3

2-N-biotinyl-N,N-dimethylethan-1,2-diamine

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 24h;100%
biotin
58-85-5

biotin

C41H56N4O7S

C41H56N4O7S

Conditions
ConditionsYield
Stage #1: biotin With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 40℃; for 0.5h; Inert atmosphere;
Stage #2: 3-{2-[2-(3-{[Bis-(4-methoxy-phenyl)-phenyl-methyl]-amino}-propoxy)-ethoxy]-ethoxy}-propylamine With triethylamine In N,N-dimethyl-formamide Inert atmosphere;
100%
N-(4-(4-(4-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethoxy)piperidin-1-yl)-2,6-dimethylphenyl)thiazol-2-yl)isonicotinamide

N-(4-(4-(4-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethoxy)piperidin-1-yl)-2,6-dimethylphenyl)thiazol-2-yl)isonicotinamide

biotin
58-85-5

biotin

N-(4-(2,6-dimethyl-4-(4-((13-oxo-17-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)-3,6,9-trioxa-12-azaheptadecyl)oxy)piperidin-1-yl)phenyl)thiazol-2-yl)isonicotinamide

N-(4-(2,6-dimethyl-4-(4-((13-oxo-17-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)-3,6,9-trioxa-12-azaheptadecyl)oxy)piperidin-1-yl)phenyl)thiazol-2-yl)isonicotinamide

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃;100%
N-(3-aminopropyl)-N-(4-chloro-2,5-dimethoxyphenyl)-4-ethoxybenzenesulfonamide hydrochloride

N-(3-aminopropyl)-N-(4-chloro-2,5-dimethoxyphenyl)-4-ethoxybenzenesulfonamide hydrochloride

biotin
58-85-5

biotin

N-(3-((N-(4-chloro-2,5-dimethoxyphenyl)-4-ethoxyphenyl)sulfonamido)propyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide

N-(3-((N-(4-chloro-2,5-dimethoxyphenyl)-4-ethoxyphenyl)sulfonamido)propyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide

Conditions
ConditionsYield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide100%
3-butene-1-amine
2524-49-4

3-butene-1-amine

biotin
58-85-5

biotin

C14H23N3O2S

C14H23N3O2S

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 24h; Inert atmosphere;100%
N-(3-aminopropyl)-N-(4-chloro-2,5-dimethoxyphenyl)-4-ethoxybenzenesulfonamide hydrochloride

N-(3-aminopropyl)-N-(4-chloro-2,5-dimethoxyphenyl)-4-ethoxybenzenesulfonamide hydrochloride

biotin
58-85-5

biotin

N-(3-((N-(4-chloro-2,5-dimethoxyphenyl)-4-ethoxyphenyl)sulfonamido)propyl)-5-((3aR,4R,6aS)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide

N-(3-((N-(4-chloro-2,5-dimethoxyphenyl)-4-ethoxyphenyl)sulfonamido)propyl)-5-((3aR,4R,6aS)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide100%
1,6-Hexanediamine
124-09-4

1,6-Hexanediamine

biotin
58-85-5

biotin

N-(6-aminohexyl)-5-((3aS,4S,6aR)-3a,6a-dimethyl-2-oxohexahydro-1H-thieno[3,4-d] imidazol-4-yl)pentanamide
65953-56-2

N-(6-aminohexyl)-5-((3aS,4S,6aR)-3a,6a-dimethyl-2-oxohexahydro-1H-thieno[3,4-d] imidazol-4-yl)pentanamide

Conditions
ConditionsYield
Stage #1: biotin With di(succinimido) carbonate; triethylamine In N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere;
Stage #2: 1,6-Hexanediamine In N,N-dimethyl-formamide Inert atmosphere;
99%
C29H37N5O4
1071926-11-8

C29H37N5O4

biotin
58-85-5

biotin

C39H51N7O6S
1071926-14-1

C39H51N7O6S

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 16h;99%
8-(6-iodo-benzo[1,3]dioxol-5-ylsulfanyl)-9-(3-isopropylamino-propyl)adenine

8-(6-iodo-benzo[1,3]dioxol-5-ylsulfanyl)-9-(3-isopropylamino-propyl)adenine

biotin
58-85-5

biotin

C28H35IN8O4S2
1418215-37-8

C28H35IN8O4S2

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 9h; Sonication; Inert atmosphere;99%
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 9h; Sonication;99%
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 9h; Sonication;99%
ethylenediamine
107-15-3

ethylenediamine

biotin
58-85-5

biotin

N-(2-aminoethyl)-5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl)pentanamide

N-(2-aminoethyl)-5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl)pentanamide

Conditions
ConditionsYield
Stage #1: biotin With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 48 - 63℃; for 0.583333 - 0.666667h;
Stage #2: ethylenediamine In N,N-dimethyl-formamide for 72h;
99%
2,3,4,5,6-pentafluorophenol
771-61-9

2,3,4,5,6-pentafluorophenol

biotin
58-85-5

biotin

biotin pentafluorophenyl ester
120550-35-8

biotin pentafluorophenyl ester

Conditions
ConditionsYield
With pyridine; dicyclohexyl-carbodiimide 0-5 deg C, 2.5 h; room temperature, 16 h;98%
With pyridine; dicyclohexyl-carbodiimide at 20 - 50℃;95%
With pyridine; 2`,3`-dideoxycytidine at 20℃; for 24h;93%
octanol
111-87-5

octanol

biotin
58-85-5

biotin

biotin octan-1-ol ester

biotin octan-1-ol ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 48h; Heating;98%
2-[2-(2-azidoethoxy)ethoxy]ethanol
86520-52-7

2-[2-(2-azidoethoxy)ethoxy]ethanol

biotin
58-85-5

biotin

C16H27N5O5S
1085938-08-4

C16H27N5O5S

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere;98%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 60℃; for 24h; Inert atmosphere;65%
acetyl chloride
75-36-5

acetyl chloride

biotin
58-85-5

biotin

biotin methyl ester
608-16-2

biotin methyl ester

Conditions
ConditionsYield
Stage #1: acetyl chloride In methanol at 0℃; for 0.25h;
Stage #2: biotin In methanol at 20℃; for 0.5h;
98%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Fmoc-Trp-OH
35737-15-6

Fmoc-Trp-OH

Fmoc-Lys-OH
105047-45-8

Fmoc-Lys-OH

Fmoc-D-Phe-OH
86123-10-6

Fmoc-D-Phe-OH

(9-fluorenylmethoxycarbonyl)-L-histidine
116611-64-4

(9-fluorenylmethoxycarbonyl)-L-histidine

biotin
58-85-5

biotin

C56H70N14O8S

C56H70N14O8S

Conditions
ConditionsYield
Stage #1: Fmoc-Lys-OH With dmap; diisopropyl-carbodiimide In N,N-dimethyl-formamide for 4h;
Stage #2: With piperidine In N,N-dimethyl-formamide for 0.166667h;
Stage #3: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; Fmoc-Trp-OH; Fmoc-D-Phe-OH; (9-fluorenylmethoxycarbonyl)-L-histidine; biotin Further stages;
98%
N-(2-(2-(2-aminoethoxy)ethoxy)ethyl)-2,4-dinitroaniline
929521-54-0

N-(2-(2-(2-aminoethoxy)ethoxy)ethyl)-2,4-dinitroaniline

biotin
58-85-5

biotin

C22H32N6O8S

C22H32N6O8S

Conditions
ConditionsYield
Stage #1: biotin With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide
Stage #2: N-(2-(2-(2-aminoethoxy)ethoxy)ethyl)-2,4-dinitroaniline In N,N-dimethyl-formamide for 0.166667h;
98%
4-azidoaniline
14860-64-1

4-azidoaniline

biotin
58-85-5

biotin

N-(4-azidophenyl)biotinamide

N-(4-azidophenyl)biotinamide

Conditions
ConditionsYield
Stage #1: biotin With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0℃; Inert atmosphere;
Stage #2: 4-azidoaniline In N,N-dimethyl-formamide at 0 - 20℃; for 2h; Inert atmosphere;
98%
bis(pentafluorophenyl)carbonate
59483-84-0

bis(pentafluorophenyl)carbonate

biotin
58-85-5

biotin

biotin pentafluorophenyl ester
120550-35-8

biotin pentafluorophenyl ester

Conditions
ConditionsYield
With 4-methyl-morpholine In N,N-dimethyl-formamide for 2h;97%
biotin
58-85-5

biotin

5-((3aS,4S,6aR)-5-oxido-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid
23015-53-4

5-((3aS,4S,6aR)-5-oxido-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid

Conditions
ConditionsYield
With sodium peroxoborate tetrahydrate; acetic acid at 20℃; for 1.33333h;97%
With dihydrogen peroxide In acetic acid for 12h; Ambient temperature;
di-tert-butyl 4-<2-(tert-butoxycarbonyl)ethyl>-4-nitroheptanedicarboxylate
136587-00-3

di-tert-butyl 4-<2-(tert-butoxycarbonyl)ethyl>-4-nitroheptanedicarboxylate

biotin
58-85-5

biotin

Biotinamidotris[2-(tert-butoxycarbonyl)ethyl]methane
353737-53-8

Biotinamidotris[2-(tert-butoxycarbonyl)ethyl]methane

Conditions
ConditionsYield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 13h;97%

58-85-5Relevant academic research and scientific papers

SYSTEMS AND METHODS FOR DETECTION OF TARGET ANALYTES USING SELECTIVELY CLEAVABLE BONDS

-

, (2021/09/10)

The invention described herein is directed to methods of isolation and detection of target analytes in a sample. The target analytes are coupled to analyte detection particles which comprise base particles having labels and affinity agents coupled thereto by linker arms. The linker arms form bonds with the labels and target analytes and are cleavable under different label and affinity cleavable conditions. Systems and methods for preparing and using the analyte detection particles are also disclosed.

METHOD FOR PRODUCING BIOTIN

-

Paragraph 0067-0083, (2021/02/25)

To provide a production method for obtaining high-purity biotin at good yields.SOLUTION: A method for producing biotin includes a process in which a composition comprising biotin represented by the formula (I) is brought into contact with hydrosulfite salt, before the biotin is extracted.SELECTED DRAWING: None

Solution Dynamics of Hybrid Anderson-Evans Polyoxometalates

Salazar Marcano, David E.,Lentink, Sarah,Moussawi, Mhamad A.,Parac-Vogt, Tatjana N.

supporting information, p. 10215 - 10226 (2021/05/31)

Understanding the stability and speciation of metal-oxo clusters in solution is essential for many of their applications in different areas. In particular, hybrid organic-inorganic polyoxometalates (HPOMs) have been attracting increasing attention as they combine the complementary properties of organic ligands and metal-oxygen nanoclusters. Nevertheless, the speciation and solution behavior of HPOMs have been scarcely investigated. Hence, in this work, a series of HPOMs based on the archetypical Anderson-Evans structure, δ-[MnMo6O18{(OCH2)3C-R}2]3-, with different functional groups (R = -NH2, -CH3, -NHCOCH2Cl, -NCH(2-C5H4N) {pyridine; -Pyr}, and -NHCOC9H15N2OS {biotin; -Biot}) and countercations (tetrabutylammonium {TBA}, Li, Na, and K) were synthesized, and their solution behavior was studied in detail. In aqueous solutions, decomposition of HPOMs into the free organic ligand, [MoO4]2-, and free Mn3+ was observed over time and was shown to be highly dependent on the pH, temperature, and nature of the ligand functional group but largely independent of ionic strength or the nature of the countercation. Furthermore, hydrolysis of the amide and imine bonds often present in postfunctionalized HPOMs was also observed. Hence, HPOMs were shown to exhibit highly dynamic behavior in solution, which needs to be carefully considered when designing HPOMs, particularly for biological applications.

Selective modification of sulfamidate-containing peptides

Busto, Jesús H.,Jiménez-Osés, Gonzalo,Mazo, Nuria,Navo, Claudio D.,Peregrina, Jesús M.

supporting information, p. 6265 - 6275 (2020/09/07)

Hybrid peptides whose N-terminal residues are activated in the form of α-methylisoserine-derived cyclic sulfamidates exhibit rich reactivity as electrophiles, allowing site- and stereoselective modifications at different backbone and side chain positions.

Synthesis method of d-biotin

-

, (2019/04/04)

The invention discloses a synthesis method of d-biotin. The synthesis method comprises the following steps: taking cysteine hydrochloride, benzaldehyde and benzyl isocyanate as starting materials, andsubjecting the starting materials to condensation, cyclization, reduction, condensation, oxidation, reduction, cyclization, elimination, catalytic hydrogenation and debenzylation sequentially to obtain the d-biotin. The method has the advantages that the raw materials are cheap and easy to obtain, the safety is good, the reaction conditions are mild and easy to control, the production cost is lowered, green and environmental protection is achieved, the reaction yield is high, separation is easy, and the purity of the obtained d-biotin is high.

Method for catalytic synthesis of biotin by using high-recycling-activity palladium-carbon catalyst

-

Paragraph 0019; 0020-0057, (2019/04/10)

The invention discloses a method for catalytic synthesis of biotin by using a high-recycling-activity palladium-carbon catalyst. The method comprises the following steps: palladium-carbon is taken asa catalyst to catalyze synthesis of biotin by hydrogenation of a biotin intermediate cis-2-oxo-1,3-dibenzyl-4-(4-carboxybutyl-1-ene)hexahydro-1H-thieno[3,4-d]imidazole, wherein activated carbon is taken as a carrier of the catalyst, the carrier is activated by hydrogen peroxide after being subjected to high-temperature treatment in an ammonia atmosphere, and then the pretreated activated carbon isobtained; the soluble palladium compound is dissolved in water, a nitrogen-containing compound is added, and reflux stirring is carried out to obtain a palladium precursor solution; and the pretreated activated carbon is pulped by using alcohol water, then a palladium precursor solution is added, an alkali is added for controlling the pH value of the system to be 6-12, and then reduction is carried out by a reducing agent to obtain the palladium-carbon catalyst. Compared with the prior art, the method disclosed by the invention has the advantages that activity of the catalyst is high, performance of the catalyst is stable, the number of recycling times in biotin synthesis can be greatly increased, and production cost can be reduced.

A preparation method of d - biotin (by machine translation)

-

Paragraph 0037; 0038; 0039; 0040; 0041; 0042; 0043-0060, (2019/05/04)

The invention belongs to the field of organic synthesis, in particular relates to a preparation method of d - biotin, the method comprises the following steps: the double-benzyl biotin with three boron halide and organic solution, in the absence of the organic solvent in the water environment, under the protection of inert gas, through the one-step reaction to remove the double-benzyl, get d - biotin. The present invention provides a simple and convenient, safe, high yield, high purity of methylsulphonyl preparation method of d - biotin, is suitable for industrial production. (by machine translation)

A dibenzyl biotin by d - biotin method of preparation

-

Paragraph 0033-0038, (2019/02/26)

The invention discloses a method for preparing d-biotin from dibenzyl biotin. The method comprises the following steps: 1, adding an inorganic acid and zinc powder to an aqueous solution of dibenzyl biotin; and 2, reacting at 40-70DEG C, and post-processing after the raction ends to obtain d-biotin. The d-biotin is prepared through removing benzyl groups by using the zinc powder/inorganic acid system under mild conditions, so the method has the advantages of simple operation and easy industrialization; and the purity of the obtained d-biotin is greater than 99.5%, and the mole yield of the obtained d-biotin is greater than 90%, so compared with the prior art, the method has substantial progress.

Method for Producing Intermediate of Biotin and Method for Producing Biotin

-

, (2020/01/08)

In the method, a trione compound represented by the following formula (1) is (i) reduced by NaAlH2(OCH2CH2OCH3)2 and subsequently further reduced by a metal borohydride salt, or (ii) reduced by calcium borohydride, thereby producing an amide alcohol compound represented by the following formula (3) (wherein, R1 and R2 may be the same or different and each represents a hydrogen atom or a protecting group of an ureylene group; R4 represents an alkyl group, an aralkyl group, or an aryl group; and each of R5, R6, and R7 represents a hydrogen atom, an alkyl group, an alkoxy group, or a halogen atom).

Selective Modification of Ribosomally Synthesized and Post-Translationally Modified Peptides (RiPPs) through Diels–Alder Cycloadditions on Dehydroalanine Residues

de Vries, Reinder H.,Viel, Jakob H.,Oudshoorn, Ruben,Kuipers, Oscar P.,Roelfes, Gerard

supporting information, p. 12698 - 12702 (2019/09/12)

We report the late-stage chemical modification of ribosomally synthesized and post-translationally modified peptides (RIPPs) by Diels–Alder cycloadditions to naturally occurring dehydroalanines. The tail region of the thiopeptide thiostrepton could be modified selectively and efficiently under microwave heating and transition-metal-free conditions. The Diels–Alder adducts were isolated and the different site- and endo/exo isomers were identified by 1D/2D 1H NMR. Via efficient modification of the thiopeptide nosiheptide and the lanthipeptide nisin Z the generality of the method was established. Minimum inhibitory concentration (MIC) assays of the purified thiostrepton Diels–Alder products against thiostrepton-susceptible strains displayed high activities comparable to that of native thiostrepton. These Diels–Alder products were also subjected successfully to inverse-electron-demand Diels–Alder reactions with a variety of functionalized tetrazines, demonstrating the utility of this method for labeling of RiPPs.

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