156017-42-4

Basic information

• Product Name: L-Alanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-3-iodo-, methyl ester
• CAS NO: 156017-42-4
• Molecular Formula: C19H18INO4
• Molecular Weight: 451.261
• Mol File: 156017-42-4.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: L-Alanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-3-iodo-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Alanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-3-iodo-, methyl ester(156017-42-4)
• EPA Substance Registry System: L-Alanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-3-iodo-, methyl ester(156017-42-4)

Safety Data

• Hazardous Substances Data: 156017-42-4(Hazardous Substances Data)

Usage

General Description

L-Alanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-3-iodo-, methyl ester is a chemical compound that consists of L-Alanine, a non-essential amino acid, and a fluorenylmethoxycarbonyl (Fmoc) protecting group attached to a methyl ester. The presence of the 3-iodo group makes this compound potentially useful in synthetic chemistry as a building block for constructing more complex molecules. The Fmoc protecting group is commonly used in peptide synthesis to protect the amine group of amino acids, allowing for selective deprotection and subsequent chemical reactions. L-Alanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-3-iodo-, methyl ester has potential applications in the fields of biochemistry, pharmaceuticals, and organic synthesis.

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 73724-45-5 N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 229962-91-8 methyl (2S)-2-(((9H-fluoren-9-ylmethoxy)carbonyl)amino)-3-(((4-methylbenzene)sulfonyl)oxy)propanoate 
• 82911-78-2 N-[(9-fluorenylmethoxy)carbonyl]-L-serine methyl ester 

Downstream Products

• 150308-80-8 N-(9-fluorenylmethoxycarbonyl)-Se-(p-methoxyphenylmethyl)-L-selenocysteine 
• 1365284-58-7 Fmoc-Sec(Mob)-OMe 
• 156017-45-7 (S)-2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}-3-{4-[(diethoxyphosphoryl)difluoromethyl]phenyl}propanoic acid 
• 282734-37-6 (2S)-2-(fluorenylmethoxycarbonylamino)-3-(5'-bromo-2'-pyridyl)propionic acid 
• 185379-40-2 (2S)-(N-fluorenylmethoxycarbonylamino)-3-(pyrid-2'-yl)propionic acid 
• 156017-44-6 Fmoc-(4-diethyl phosphonodifluoromethyl)-Phe-OMe 
• 1360157-23-8 (S)-methyl-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-(N,N-bis(2,4-dimethoxybenzyl)sulfamoyl)-1-trityl-1H-imidazol-2-yl)propanoate 

Relevant articles and documents

Crystal (6S,9aS)-N-benzyl-8-({6-[3-(4-ethylpiperazin-1-yl)azetidin-1-yl]pyridin-2-yl}methyl)-6-(2-fluoro-4-hydroxybenzyl)-4,7-dioxo-2-(prop-2-en-1-yl)hexahydro-2H-pyrazino[2,1-c][1,2,4]triazine-1(6H)-carboxamide

The present invention provides a crystal of (6S,9aS)-N-benzyl-8-({6-[3-4-ethylpiperazin-1-yl)azetidin-1-yl]pyridin-2-yl} methyl)-6-(2-fluoro-4-hydroxybenzyl)-4,7-dioxo-2-(prop-2-en-1-yl)hexahydro-2H-pyrazino[2,1-c][1,2,4]triazine-1(6H)-carboxamide.

(6S,9aS)-N-Benzyl-6-[(4-hydroxyphenyl)methyl]-4,7-dioxo-8-(methyl)-2-(prop-2-en-1-yl)-octahydro-1H-pyrazino[2,1-c][1,2,4]triazine-1-carboxamide compound

A compound represented by formula (1) or pharmaceutically acceptable salt thereof: wherein R1 is a C1-6 alkyl group; R2 and R3 are the same or different from each other and each is a hydrogen atom or a C1-6 alkyl group; X2, X3 and X4 are the same or different from each other and each is a hydrogen atom or a halogen atom; and X5 is a hydrogen atom or —P(═O)(OH)2 has a Wnt Pathway modulating activity.

Strain-Promoted Reaction of 1,2,4-Triazines with Bicyclononynes

Strain-promoted inverse electron-demand Diels-Alder cycloaddition (SPIEDAC) reactions between 1,2,4,5-tetrazines and strained dienophiles, such as bicyclononynes, are among the fastest bioorthogonal reactions. However, the synthesis of 1,2,4,5-tetrazines is complex and can involve volatile reagents. 1,2,4-Triazines also undergo cycloaddition reactions with acyclic and unstrained dienophiles at elevated temperatures, but their reaction with strained alkynes has not been described. We postulated that 1,2,4-triazines would react with strained alkynes at low temperatures and therefore provide an alternative to the tetrazine cycloaddition reaction for use in in vitro or in vivo labelling experiments. We describe the synthesis of a 1,2,4-triazin-3-ylalanine derivative fully compatible with the fluorenylmethyloxycarbonyl (Fmoc) strategy for peptide synthesis and demonstrate its reaction with strained bicyclononynes at 37°C with rates comparable to the reaction of azides with the same substrates. The synthetic route to triazinylalanine is readily adaptable to late-stage functionalization of other probe molecules, and the 1,2,4-triazine-SPIEDAC therefore has potential as an alternative to tetrazine cycloaddition for applications in cellular and biochemical studies.