Fmoc-β-(2-thienyl)-D-alanine
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Fmoc-β-(2-thienyl)-D-alanine

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Category
Fmoc-Amino Acids
Catalog number
BAT-007500
CAS number
201532-42-5
Molecular Formula
C22H19NO4S
Molecular Weight
393.46
Fmoc-β-(2-thienyl)-D-alanine
IUPAC Name
(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-thiophen-2-ylpropanoic acid
Synonyms
Fmoc-3-D-Ala(2-thienyl)-OH; (R)-N-Fmoc-2-thienylalanine
Related CAS
130309-35-2 (L-isomer)
Appearance
White powder
Purity
≥ 98% (HPLC)
Density
1.343 g/cm3
Melting Point
164-173 °C
Boiling Point
623.4°C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C22H19NO4S/c24-21(25)20(12-14-6-5-11-28-14)23-22(26)27-13-19-17-9-3-1-7-15(17)16-8-2-4-10-18(16)19/h1-11,19-20H,12-13H2,(H,23,26)(H,24,25)/t20-/m1/s1
InChI Key
PXBMQFMUHRNKTG-HXUWFJFHSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CC=CS4)C(=O)O

Fmoc-β-(2-thienyl)-D-alanine, a versatile protected amino acid derivative, finds extensive utility in peptide synthesis and biochemical research. Here are the key applications of Fmoc-β-(2-thienyl)-D-alanine, presented with high perplexity and burstiness:

Peptide Synthesis: Positioned at the forefront of solid-phase peptide synthesis, Fmoc-β-(2-thienyl)-D-alanine plays a pivotal role in crafting intricate peptides. Its thienyl side chain introduces a realm of structural diversity, enhancing the biological potency of synthetic peptides. This amino acid derivative is indispensable for fabricating peptides endowed with heightened binding properties and unparalleled specificity.

Drug Development: Stepping into the realm of pharmaceutical advancements, Fmoc-β-(2-thienyl)-D-alanine is integrated into peptide drug candidates to fine-tune their pharmacological characteristics. The rigid molecular structure of this compound stabilizes peptide conformations, fortifying their resilience against enzymatic breakdown. The outcome is a cohort of peptides boasting enhanced therapeutic efficacy and prolonged half-lives within the biological milieu.

Protein-Protein Interaction Studies: Embarked on unraveling the intricacies of protein interactions, researchers harness Fmoc-β-(2-thienyl)-D-alanine in designing peptide-based probes. The distinctive electronic attributes of the thienyl moiety exert a profound influence on the binding affinity of peptides towards target proteins. This strategic deployment aids in deciphering molecular dialogues and pinpointing novel druggable targets.

Material Science: Venturing into the domain of materials innovation, Fmoc-β-(2-thienyl)-D-alanine contributes to the fabrication of bio-functional materials. Its integration into peptide-based hydrogels or nanomaterials elevates the biocompatibility and functionality of these constructs. This advancement holds promise for the creation of cutting-edge biomaterials catering to applications in tissue engineering and drug delivery systems.

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