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

Chemical Properties

White to off-white crystals

Uses

FMOC-HIS(MMT)-OH (CAS# 133367-33-6) is used in the preparation of fluorophore ATCUN complexes, a probe for oxidative DNA cleavage.

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;

...Expand

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;

...Expand

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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