146346-82-9

Basic information

• Product Name: FMOC-THR(TBDMS)-OH
• Synonyms: FMOC-L-THR(TBDMS)-OH;FMOC-THR(TBDMS)-OH;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-O-(TERT-BUTYL-DIMETHYLSILYL)-L-THREONINE;fmoc-o-(tert.-butyldimethylsilyl)-l-threonine;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-O-(T-BUTYL-DIMETHYLSILYL)-L-THREONINE;N-ALPHA-(9-FLUOROENYLMETHYLOXYCARBONYL)-O-(T-BUTYL-DIMETHYLSILYL)-L-THREONINE;O-[(1,1-Dimethylethyl)dimethylsilyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-threonine;(9H-Fluoren-9-yl)MethOxy]Carbonyl Thr(TBDMS)-OH
• CAS NO: 146346-82-9
• Molecular Formula: C₂₅H₃₃NO₅Si
• Molecular Weight: 455.62
• Product Categories: Amino Acids
• Mol File: 146346-82-9.mol

Chemical Properties

• Boiling Point: 577.2±50.0 °C(Predicted)
• Appearance: /
• Density: 1.136±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 3.38±0.10(Predicted)
• BRN: 5888824
• CAS DataBase Reference: FMOC-THR(TBDMS)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-THR(TBDMS)-OH(146346-82-9)
• EPA Substance Registry System: FMOC-THR(TBDMS)-OH(146346-82-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 146346-82-9(Hazardous Substances Data)

Usage

Uses

Used in Peptide Synthesis:
FMOC-THR(TBDMS)-OH is used as a protected amino acid building block for the synthesis of peptides. The protective groups ensure that the threonine residue remains intact and unreacted during the assembly of the peptide chain, facilitating the controlled addition of amino acids.
Used in Solid-Phase Peptide Synthesis (SPPS):
In solid-phase peptide synthesis, FMOC-THR(TBDMS)-OH serves as a key component, where the protective groups allow for the stepwise elongation of the peptide chain on an insoluble resin support. The FMOC group can be selectively removed to expose the amino group for further reactions, while the TBDMS group protects the hydroxyl group of threonine from unwanted side reactions.
Used in Organic Chemistry:
FMOC-THR(TBDMS)-OH is utilized in various organic chemistry applications, particularly where selective protection of functional groups is required. FMOC-THR(TBDMS)-OH can be employed in the synthesis of complex organic molecules, where the controlled deprotection of the threonine amino acid and the hydroxyl group allows for the introduction of other functional groups or structural motifs.
Used in Pharmaceutical and Biochemical Research:
FMOC-THR(TBDMS)-OH is used as a protected amino acid in the development of new pharmaceutical compounds and in biochemical research. FMOC-THR(TBDMS)-OH can be incorporated into drug candidates or used to study the role of threonine in biological processes, with the protective groups ensuring the stability and reactivity of the molecule during experimentation.

Upstream product

• 71989-35-0 Fmoc-Thr(tBu)-OH 
• 73731-37-0 Fmoc-Thr-OH 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 104197-64-0 O-(tert-butyldimethylsilyloxy)-L-threonine 

Downstream Products

• 915098-73-6 C₆₄H₉₃N₁₁O₂₈P₂Si₂ 
• 915098-66-7 Alloc-Gly-Ala-Tyr-Thr(TBS)-Gly-OH 
• 1240360-55-7 Z-Phe-Ala-Thr(TBS)-Met-Arg(Tos)-Tyr(Pen)-Pro-Ser(tBu)-Asp(OAll)-Ser(Bzl)-Asp(OtBu)-OH 

Relevant articles and documents

Synthesis of autophagosomal marker protein LC3-II under detergent-free conditions

Just add oil: A new detergent-free method was developed to synthesize lipidated proteins using a light-activatable solubilizing side chain (in dashed circle, see scheme) to assist the ligation of the lipopeptides. This method allows the efficient preparation of a phosphatidylethanolamine-conjugated autophagosomal marker protein (LC3-II) as well as labeled derivatives of LC3-II, which can be used to study autophagy regulation. Copyright

General Fmoc-Based Solid-Phase Synthesis of Complex Depsipeptides Circumventing Problematic Fmoc Removal

Development of an Fmoc-based solid-phase depsipeptide methodology has been hampered by base-promoted fragmentation and diketoperazine formation upon Fmoc group elimination. Such a strategy would be a useful tool given the number of commercially available Fmoc-protected residues. Herein we report that the addition of small percentages of organic acids to the Fmoc-removal cocktail proves effective to circumvent these drawbacks and most importantly, allowed the development of an exclusively solid-phase stepwise methodology to prepare a highly complex depsipeptide with multiple and consecutive esters bonds. Alongside, the optimal protecting group scheme for residue incorporation, which is not as straightforward as it is for traditional peptide synthesis, was explored. The developed stepwise strategy proved effective for the synthesis of a highly complex cyclodepsipeptide, being comparable to the yields obtained when using traditional combined chemistry approaches.

Synthesis of N-protected N-methyl serine and threonine

Two efficient and convenient syntheses of N-Cbz and N-Fmoc N-methyl serine and threonine are described. The amino acid side-chain alcohol can be protected as a TBDMS ether in very good yield or left free, followed by the formation and subsequent reduction of the corresponding oxazolidinone.

Mild, selective cleavage of amino acid and peptide β-(trimethylsilyl)ethoxymethyl (SEM) esters by magnesium bromide

Magnesium bromide etherate has been previously shown to cleave β-(trimethylsilyl)ethoxymethyl (SEM) esters of aliphatic acids. This methodology has now been extended to amino acid and peptide derivatives in the presence of protecting groups typically encountered in peptide chemistry, including the Boc, Cbz, Fmoc and Troc carbamates as well as benzyl-, tert-butyl- and tert-butyldimethylsilyl ethers. The stability of fluoride sensitive protecting groups to magnesium bromide allows for added selectivity in the removal of SEM esters in organic synthesis.

Application of t-Butyldimethylsilyl Ethers of Serine, Threonine and Tyrosine in Peptide Synthesis

The utility of Tbdms (t-butyldimethylsilyl) ethers, prepared conveniently in a one pot procedure from Nα-Fmoc (9-fluorenylmethoxycarbonyl) and Nα-Z (benzyloxycarbonyl) hydroxyamino acids, is demonstrated: peptide bond formation and esterification to 4-alkoxybenzylalcohol resin are achieved readily with these derivatives.The lability of the Tbdms ethers to various reagents enables selective deprotection of the hydroxyl side-chains assembly, desirable, e.g., for phosphorylation of glycosylation.