133367-33-6

Basic information

• Product Name: FMOC-HIS(MMT)-OH
• Synonyms: N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-N-TAU-4-METHOXYTRITYL-L-HISTIDINE;FMOC-L-HIS(MMT)-OH;FMOC-HIS(MEOTRT)-OH;FMOC-HIS(MMT)-OH;FMOC-NIM-(4-METHOXYTRITYL)-L-HISTIDINE;FMOC-N-IM-METHOXYTRITYL-L-HISTIDINE;N-ALPHA-(9-FLUOROENYLMETHYLOXYCARBONYL)-N-IM-P-METHOXYTRITYL-L-HISTIDINE;(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)((4-methoxyphenyl)diphenylmethyl)amino)-3-(1H-imidazol-4-yl)propanoic acid
• CAS NO: 133367-33-6
• Molecular Formula: C41H35N3O5
• Molecular Weight: 649.73
• Product Categories: Amino Acids;Fmoc-Amino Acids and Derivatives;Fmoc-Amino acid series
• Mol File: 133367-33-6.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 835.665 °C at 760 mmHg
• Flash Point: 459.194 °C
• Appearance: /
• Density: 1.24±0.1 g/cm3 (20 ºC 760 Torr)
• Refractive Index: 1.647
• Storage Temp.: Store at 0°C
• CAS DataBase Reference: FMOC-HIS(MMT)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-HIS(MMT)-OH(133367-33-6)
• EPA Substance Registry System: FMOC-HIS(MMT)-OH(133367-33-6)

Safety Data

• Hazardous Substances Data: 133367-33-6(Hazardous Substances Data)

Usage

Description

FMOC-HIS(MMT)-OH, with the chemical name 9-fluorenylmethoxycarbonyl-L-histidine(1-(4-methoxyphenyl)-1H-1,2,3-triazole-4-ylmethyl)ester, is a synthetic compound characterized by its white to off-white crystalline appearance. It is a derivative of L-histidine, a naturally occurring amino acid, and is modified with a 9-fluorenylmethoxycarbonyl (Fmoc) protecting group and a 1,2,3-triazole linker. This unique structure endows FMOC-HIS(MMT)-OH with specific chemical properties that make it suitable for various applications in different fields.

Uses

Used in Chemical Synthesis:
FMOC-HIS(MMT)-OH is used as a key intermediate in the synthesis of fluorophore ATCUN complexes, which serve as probes for the detection and study of oxidative DNA cleavage. FMOC-HIS(MMT)-OH's ability to form stable complexes with fluorophores and its reactivity in the presence of oxidative agents make it an essential component in the development of these analytical tools.
Used in Biochemistry Research:
In the field of biochemistry, FMOC-HIS(MMT)-OH is utilized for the investigation of DNA-protein interactions and the mechanisms of oxidative stress on DNA. Its role in the formation of ATCUN complexes allows researchers to monitor and analyze the effects of oxidative agents on DNA integrity, providing valuable insights into the molecular processes underlying various diseases and conditions.
Used in Pharmaceutical Development:
FMOC-HIS(MMT)-OH also holds potential in the pharmaceutical industry, particularly in the development of drugs targeting oxidative stress-related diseases. Its involvement in the synthesis of ATCUN complexes can contribute to the discovery of new therapeutic agents capable of modulating oxidative processes and protecting DNA from damage.

InChI:InChI=1/C41H35N3O5/c1-48-32-22-20-30(21-23-32)41(28-12-4-2-5-13-28,29-14-6-3-7-15-29)44-25-31(42-27-44)24-38(39(45)46)43-40(47)49-26-37-35-18-10-8-16-33(35)34-17-9-11-19-36(34)37/h2-23,25,27,37-38H,24,26H2,1H3,(H,43,47)(H,45,46)/t38-/m0/s1

Synthetic route

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Val-OH (68858-20-8) + Fmoc-Leu-OH (35661-60-0) + Fmoc-His(Mmt)-OH (133367-33-6) + C34H39N4O7PolS + Fmoc-Ser(tBu)-OH (71989-33-8) → Val-Gly-Gly-Leu-Ser-His-Arg

Conditions

Yield

Stage #1: C34H39N4O7PolS With piperidine In N,N-dimethyl-formamide 2-chlorotrityl chloride resin; Stage #2: Fmoc-His(Mmt)-OH With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 1h; 2-chlorotrityl chloride resin; Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Val-OH; Fmoc-Leu-OH; Fmoc-Ser(tBu)-OH Further stages;

26%

aminomethyl-terminated Tentagel resin + L-valine (72-18-4) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3) + Fmoc-His(Mmt)-OH (133367-33-6) + Fmoc-O-trityl-l-threonine (133180-01-5) + (2S)-N-allyloxycarbonyl-L-proline (110637-44-0) + [4-(hydroxymethyl)phenoxy]acetic acid (68858-21-9) + Fmoc-Ser(Trt)-OH (111061-56-4) + glycine (56-40-6) + (N-tritylaminooxy)acetic acid (112257-05-3) → C38H60N12O14 (1616473-90-5)

Conditions

Yield

Stage #1: aminomethyl-terminated Tentagel resin; [4-(hydroxymethyl)phenoxy]acetic acid 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 for 2h; aminomethyl polyethylene glycol polyacrylamide resin; Automated synthesizer; Stage #2: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide for 2h; aminomethyl polyethylene glycol polyacrylamide resin; Automated synthesizer; Stage #3: L-valine; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; Fmoc-His(Mmt)-OH; Fmoc-O-trityl-l-threonine; (2S)-N-allyloxycarbonyl-L-proline; Fmoc-Ser(Trt)-OH; glycine; (N-tritylaminooxy)acetic acid Further stages;

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N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-His(Mmt)-OH (133367-33-6) + Fmoc-Asp-OAllyl + N-Fmoc L-Phe (35661-40-6) + Fmoc-Ile-OH (71989-23-6) + N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine (71989-20-3) + Fmoc-L-ArgNO2 + 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester (143824-78-6) → C56H77N19O18

Conditions

Yield

Stage #1: Fmoc-Asp-OAllyl With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.833333h; Stage #2: With piperidine In N,N-dimethyl-formamide at 20℃; for 0.183333h; Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-His(Mmt)-OH; N-Fmoc L-Phe; Fmoc-Ile-OH; N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine; Fmoc-L-ArgNO2; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester Further stages;

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N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-His(Mmt)-OH (133367-33-6) + Fmoc-Trp(BODIPY)-OH + Fmoc-Asp-OAllyl + N-Fmoc L-Phe (35661-40-6) + Fmoc-Ile-OH (71989-23-6) + N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine (71989-20-3) + Fmoc-L-ArgNO2 → C75H94BF2N21O18

Conditions	Yield
Stage #1: Fmoc-Asp-OAllyl With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.833333h; Stage #2: With piperidine In N,N-dimethyl-formamide at 20℃; for 0.183333h; Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-His(Mmt)-OH; Fmoc-Trp(BODIPY)-OH; N-Fmoc L-Phe; Fmoc-Ile-OH; N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine; Fmoc-L-ArgNO2 Further stages;

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