Nα-Fmoc-Nγ-trityl-D-asparagine
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Nα-Fmoc-Nγ-trityl-D-asparagine

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Category
Fmoc-Amino Acids
Catalog number
BAT-003677
CAS number
180570-71-2
Molecular Formula
C38H32N2O5
Molecular Weight
596.70
Nα-Fmoc-Nγ-trityl-D-asparagine
IUPAC Name
(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxo-4-(tritylamino)butanoic acid
Synonyms
Fmoc-D-Asn(Trt)-OH; (2R)-2-(9H-Fluoren-9-Ylmethoxycarbonylamino)-4-Oxo-4-(Tritylamino)Butanoic Acid
Appearance
White powder
Purity
≥ 99% (HPLC)
Density
1.271±0.06 g/cm3(Predicted)
Melting Point
203-208 °C
Boiling Point
858.1±65.0 °C(Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C38H32N2O5/c41-35(40-38(26-14-4-1-5-15-26,27-16-6-2-7-17-27)28-18-8-3-9-19-28)24-34(36(42)43)39-37(44)45-25-33-31-22-12-10-20-29(31)30-21-11-13-23-32(30)33/h1-23,33-34H,24-25H2,(H,39,44)(H,40,41)(H,42,43)/t34-/m1/s1
InChI Key
KJYAFJQCGPUXJY-UUWRZZSWSA-N
Canonical SMILES
C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)NC(=O)CC(C(=O)O)NC(=O)OCC4C5=CC=CC=C5C6=CC=CC=C46

Nα-Fmoc-Nγ-trityl-D-asparagine, a protected amino acid derivative widely utilized in peptide synthesis and biochemical research, finds diverse applications in various fields. Here are four key applications:

Peptide Synthesis: Embedded in the realm of solid-phase peptide synthesis (SPPS), Nα-Fmoc-Nγ-trityl-D-asparagine plays a pivotal role in crafting peptides of exceptional purity and precise sequences. Its Fmoc group acts as a shield for the amino group during peptide assembly, while the trityl group safeguards the side chain, offering selective removal under mildly acidic conditions. This unique feature facilitates the sequential addition of amino acids, culminating in the synthesis of intricate peptide structures.

Drug Development: A cornerstone in the synthesis of therapeutic peptides and peptidomimetics, Nα-Fmoc-Nγ-trityl-D-asparagine empowers researchers to design drug candidates with heightened stability, bioavailability, and target specificity. By incorporating this derivative into peptide-based therapies, scientists can usher in a new era of precision medicine targeting diseases ranging from cancer to infectious diseases and metabolic disorders with unparalleled efficacy.

Protein Engineering: At the forefront of protein engineering and structural studies, Nα-Fmoc-Nγ-trityl-D-asparagine emerges as a versatile tool for tailoring custom peptides. By incorporating this amino acid derivative into peptides, researchers gain the ability to introduce site-specific modifications or create stable analogs of natural proteins. These engineered peptides serve as invaluable probes for unraveling protein-protein interactions, deciphering folding mechanisms, and dissecting enzyme activities with intricate precision.

Biomaterials Research: In the realm of biomaterials for tissue engineering and regenerative medicine, Nα-Fmoc-Nγ-trityl-D-asparagine shines as a paramount component in crafting scaffolds that mimic the extracellular matrix. These peptide-based biomaterials foster cell adhesion, proliferation, and differentiation, holding immense promise for applications in wound healing, orthopedic interventions, and cardiovascular repair. With its multifaceted applications in diverse fields, this derivative drives innovation at the intersection of biochemistry and materials science.

1.Solid-Phase Total Synthesis of Bacitracin A.
Lee J1, Griffin JH, Nicas TI. J Org Chem. 1996 Jun 14;61(12):3983-3986.
An efficient solid-phase method for the total synthesis of bacitracin A is reported. This work was undertaken in order to provide a general means of probing the intriguing mode of action of the bacitracins and exploring their potential for use against emerging drug-resistant pathogens. The synthetic approach to bacitracin A involves three key features: (1) linkage to the solid support through the side chain of the L-asparaginyl residue at position 12 (L-Asn(12)), (2) cyclization through amide bond formation between the alpha-carboxyl of L-Asn(12) and the side chain amino group of L-Lys(8), and (3) postcyclization addition of the N-terminal thiazoline dipeptide as a single unit. To initiate the synthesis, Fmoc L-Asp(OH)-OAllyl was attached to a PAL resin. The chain of bacitracin A was elaborated in the C-to-N direction by sequential piperidine deprotection/HBTU-mediated coupling cycles with Fmoc D-Asp(OtBu)-OH, Fmoc L-His(Trt)-OH, Fmoc D-Phe-OH, Fmoc L-Ile-OH, Fmoc D-Orn(Boc)-OH, Fmoc L-Lys(Aloc)-OH, Fmoc L-Ile-OH, Fmoc D-Glu(OtBu)-OH, and Fmoc L-Leu-OH.
2.Chemical synthesis and receptor binding of catfish somatostatin: a disulfide-bridged beta-D-Galp-(1-->3)-alpha-D-GalpNAc O-glycopeptide.
Chen L1, Jensen KJ, Tejbrant J, Taylor JE, Morgan BA, Barany G. J Pept Res. 2000 Jan;55(1):81-91.
The glycopeptide hormone catfish somatostatin (somatostatin-22) has the amino acid sequence H-Asp-Asn-Thr-Val-Thr-Ser-Lys-Pro-Leu-Asn-Cys-Met-Asn-Tyr-Phe-Trp-Lys-Se r-Arg-Thr-Ala-Cys-OH; it includes a cyclic disulfide connecting the two Cys residues, and the major naturally occurring glycoform contains D-GalNAc and D-Gal O-glycosidically linked to Thr5. The linear sequence was assembled smoothly starting with an Fmoc-Cys(Trt)-PAC-PEG-PS support, using stepwise Fmoc solid-phase chemistry. In addition to the nonglycosylated peptide, two glycosylated forms of somatostatin-22 were accessed by incorporating as building blocks, respectively, Nalpha-Fmoc-Thr(Ac3-alpha-D-GalNAc)-OH and Nalpha-Fmoc-Thr(Ac4-beta-D-Gal-(1-->3)-Ac2-alpha-D-GalNAc)-O H. Acidolytic deprotection/cleavage of these peptidyl-resins with trifluoroacetic acid/scavenger cocktails gave the corresponding acetyl-protected glycopeptides with free sulfhydryl functions. Deacetylation, by methanolysis in the presence of catalytic sodium methoxide, was followed by mild oxidation at pH 7, mediated by Nalpha-dithiasuccinoyl (Dts)-glycine, to provide the desired monomeric cyclic disulfides.
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