130674-54-3

Basic information

• Product Name: FMOC-D-ALLO-THR-OH
• Synonyms: FMOC-D-THR(ALLO)-OH;FMOC-D-ALLO-THR-OH;FMOC-D-ALLO-THREONINE;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-D-ALLO-THREONINE;N-alpha-(9-Fluorenylmethyloxycarbonyl)-allo-D-threonine;Fmoc-D-allo-threonine99%;(9H-Fluoren-9-yl)MethOxy]Carbonyl D-Allo-Thr-OH
• CAS NO: 130674-54-3
• Molecular Formula: C₁₉H₁₉NO₅
• Molecular Weight: 341.36
• Product Categories: Amino Acids
• Mol File: 130674-54-3.mol

Chemical Properties

• Boiling Point: 596.5 °C at 760 mmHg
• Flash Point: 314.6 °C
• Appearance: /
• Density: 1.327g/cm³
• Storage Temp.: Store at RT.
• PKA: 3.49±0.10(Predicted)
• CAS DataBase Reference: FMOC-D-ALLO-THR-OH(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-D-ALLO-THR-OH(130674-54-3)
• EPA Substance Registry System: FMOC-D-ALLO-THR-OH(130674-54-3)

Safety Data

• Hazardous Substances Data: 130674-54-3(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
FMOC-D-ALLO-THR-OH is used as a building block for the synthesis of complex organic molecules, particularly in the creation of peptides and proteins. Its unique stereochemistry and protecting group facilitate the controlled assembly of these biomolecules.
Used in Biochemistry Research:
In biochemistry, FMOC-D-ALLO-THR-OH is employed as a research tool for studying the structure and function of peptides and proteins. Its D-stereoisomer and allo-threonine characteristics allow for the investigation of stereoselectivity and the impact of structural variations on biological activity.
Used in Pharmaceutical Development:
FMOC-D-ALLO-THR-OH is utilized in the development of pharmaceuticals, where its unique properties can be leveraged to create novel therapeutic agents. Its role in peptide synthesis enables the design of drugs with specific biological activities and improved pharmacokinetic profiles.
Used in Peptide Synthesis:
FMOC-D-ALLO-THR-OH is used as a protected amino acid in peptide synthesis, allowing for the stepwise assembly of peptide chains with precise control over the sequence and stereochemistry. This is crucial for the production of biologically active peptides and proteins with desired properties.
Used in Materials Science:
In materials science, FMOC-D-ALLO-THR-OH may be explored for its potential in creating novel biomaterials, such as self-assembling peptide scaffolds or hydrogels, with tailored properties for various applications, including tissue engineering and drug delivery.
Used in Analytical Chemistry:
FMOC-D-ALLO-THR-OH can be employed in the development of analytical methods for the detection and quantification of amino acids and peptides. Its unique chemical properties may be harnessed to improve the sensitivity and selectivity of these analytical techniques.

Upstream product

• 24830-94-2 D-allo-threonine 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 170643-02-4 N^α-(9-Fluorenylmethoxycarbonyl)-D-allothreonine t-butyl ether 

Downstream Products

• 72-19-5 L-threonine 
• 2812-27-3 N-methyl threonine 
• 2812-36-4 N,N-dimethyl-threonine 
• 122889-12-7 N-(9-fluorenylmethoxycarbonyl)-L-threonine pentafluorophenyl ester 
• 912557-38-1 N-maleimido-Gly-Tyr-Thr-Gly-OH 
• 170643-02-4 N^α-(9-Fluorenylmethoxycarbonyl)-D-allothreonine t-butyl ether 

Relevant articles and documents

Asymmetric synthesis of (2S,3S)-3-Me-glutamine and (R)-allo-threonine derivatives proper for solid-phase peptide coupling

Practical new routes for preparation of (2S,3S)-3-Me-glutamine and (R)-allo-threonine derivatives, the key structural components of cytotoxic marine peptides callipeltin O and Q, suitable for the Fmoc-SPPS, were developed. (2S,3S)-Fmoc-3-Me-Gln(Xan)-OH was synthesized via Michael addition reactions of Ni (II) complex of chiral Gly-Schiff base; while Fmoc-(R)-allo-Thr-OH was prepared using chiral Ni (II) complex-assisted α-epimerization methodology, starting form (S)-Thr(tBu)-OH.

Synthetic studies on callipeltins: Stereoselective syntheses of (3S,4R)-3,4-dimethyl-L-pyroglutamic acid and fmoc-D-allothreonine from serine derivatives

The non-proteinogenic amino acids contained in callipeltins, (3S, 4R)-3, 4-dimefhyl-L-pyroglutamic acid and D-allothreonine, were synthesized from D- or L-serine. The stereoselective synthesis of two methyl groups of (3S, 4R)-3, 4-dimethyl-L-pyroglutamic acid was accomplished by diastereoselective hydrogenation and alkylation. Kinetic epimerization of the C-4 methyl substituent followed by Boc-deprotection with 10% TFA gave the desired (3S, 4R)-3, 4-dimethyl-L-pyroglutamic acid as a single isomer.

Improved synthesis of d-allothreonine derivatives from l-threonine

The improved synthesis of protected d-allothreonine derivatives [Fmoc-d-alloThr(tBu)-OH (1) and Fmoc-d-alloThr-OtBu (2)] is described. The epimerization of cheap l-threonine (l-Thr) (3) with catalytic salicylaldehyde afforded a mixture of l-Thr (3) and d-alloThr (4) and separation of ammonium salt gave d-alloThr (4) in 96% de. The chemoselective deprotection of tert-butyl ether or tert-butyl ester of Fmoc-d-alloThr(tBu)-O tBu (5) easily succeeded in converting Fmoc-d-alloThr( tBu)-OH (1) or Fmoc-d-alloThr-OtBu (2), respectively.

Solid phase total synthesis of callipeltin e isolated from marine sponge Latrunculia sp.

Solid phase total synthesis of callipeltin E (1), truncated linear peptide isolated from marine sponge, Latrunculia sp. was achieved. Our strategy based on traditional Fmoc-SPPS was in common use TFA-treatment final deprotection to reach callipeltin E (1) contained acid-sensitive βMeOTyr.

Synthesis of Nα-(9-Fluorenylmethoxycarbonyl)-Allothreonine t-Butyl Ether via Threonine Oxazolines

New procedures for the preparation of allothreonine, suitably protected for solid phase peptide synthesis, were developed.Stereochemical inversion in the side chain of threonine via thionyl chloride-induced oxazoline cyclisation and subsequent hydrolysis, followed by protection of the allothreonine amino and hydroxyl functions provided Fmoc-D-alloThr(But)-OH from benzoyl-D-threonine phenacyl ester in only five steps.Alternatively, it was shown that temporary carboxyl protection for introduction of the t-butyl ether group can be circumvented by direct selective ester acidolysis from Fmoc-Thr(But)-OBut.