N-Fmoc-3-iodo-L-alanine tert-butyl ester
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N-Fmoc-3-iodo-L-alanine tert-butyl ester

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Category
Fmoc-Amino Acids
Catalog number
BAT-009036
CAS number
282734-33-2
Molecular Formula
C22H24INO4
Molecular Weight
493.33
N-Fmoc-3-iodo-L-alanine tert-butyl ester
IUPAC Name
tert-butyl (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-iodopropanoate
Synonyms
(R)-tert-Butyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-iodopropanoate
Purity
95%
InChI
InChI=1S/C22H24INO4/c1-22(2,3)28-20(25)19(12-23)24-21(26)27-13-18-16-10-6-4-8-14(16)15-9-5-7-11-17(15)18/h4-11,18-19H,12-13H2,1-3H3,(H,24,26)/t19-/m0/s1
InChI Key
WFECRYMZJXNQQC-IBGZPJMESA-N
Canonical SMILES
CC(C)(C)OC(=O)C(CI)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

N-Fmoc-3-iodo-L-alanine tert-butyl ester, a specialized chemical compound with diverse applications in biotechnology and pharmaceuticals, is a versatile building block for various cutting-edge endeavors. Here are the key applications presented with high perplexity and burstiness:

Peptide Synthesis: Serving as a cornerstone in solid-phase peptide synthesis (SPPS), N-Fmoc-3-iodo-L-alanine tert-butyl ester plays a crucial role in incorporating iodine into peptide chains, facilitating post-synthetic modifications and the intricate construction of peptides adorned with desired functional groups. The tert-butyl ester acts as a guardian, safeguarding the carboxyl group throughout synthesis, ensuring precise chain elongation and the production of impeccably pure final peptide products.

Medicinal Chemistry: Embedded at the core of medicinal chemistry, this compound emerges as a foundational element for designing and synthesizing bioactive molecules. The iodine atom acts as a springboard for further functionalization or radiolabeling, aiding in the development of diagnostic agents and therapeutic drugs that redefine healthcare landscapes. Scientists rely on N-Fmoc-3-iodo-L-alanine tert-butyl ester to engineer molecules with tailored pharmacological properties, steering drug discovery into uncharted territories of innovation.

Protein Engineering: Unveiling new dimensions within protein engineering, N-Fmoc-3-iodo-L-alanine tert-butyl ester empowers the integration of non-natural amino acids into proteins, unveiling unexplored protein structure-function relationships and enabling the creation of proteins with unprecedented properties. By incorporating iodine-labeled amino acids, researchers harness sophisticated imaging techniques to delve deep into protein dynamics and interactions, unraveling the intricate tapestry of protein behavior in a realm of boundless possibilities.

Organic Synthesis: Transcending biological frontiers, N-Fmoc-3-iodo-L-alanine tert-butyl ester finds its niche in organic synthesis for crafting complex organic compounds of extraordinary sophistication. Its flexibility in reactivity and protection group strategy renders it an indispensable intermediate for synthesizing a diverse array of molecules. Organic chemists leverage this compound to innovate materials, catalysts, and other specialized chemicals for a multitude of industrial applications, propelling the evolution of organic synthesis methodologies into realms of unparalleled creativity and advancement.

1. Di-tert-butyl (2R,3R)-2-{[(2E)-3-(4-acet-yloxy-3-meth-oxy-phen-yl)prop-2-eno-yl]-oxy}-3-hy-droxy-butane-dioate
Josh L Hixson, Dennis K Taylor, Seik Weng Ng, Edward R T Tiekink Acta Crystallogr Sect E Struct Rep Online. 2012 Mar 1;68(Pt 3):o568-9. doi: 10.1107/S1600536812002784. Epub 2012 Feb 4.
In the title mol-ecule, C(24)H(32)O(10), one tert-butyl ester group is folded towards the central benzene ring while the other is directed away. The acetyl group is almost perpendicular to the benzene ring to which it is connected [C-C-O-C torsion angle = 90.4 (12)°]. The conformation about the ethene bond [1.313 (7) Å] is E. The atoms of the benzene ring and its attached ester group and part of the hy-droxy tert-butyl ester side chain are disordered over two sets of sites in a 50:50 ratio. Linear supra-molecular chains along the a axis mediated by hy-droxy-carbonyl O-H⋯O hydrogen bonds feature in the crystal packing. The same H atom also partakes in an intra-molecular O-H⋯O inter-action.
2. Phenyl 3,5-di-tert-butyl-2-hy-droxy-benzoate
Alexander Carreño, Marcelo Preite, Juan Manuel Manriquez, Andrés Vega, Ivonne Chavez Acta Crystallogr Sect E Struct Rep Online. 2010 Nov 24;66(Pt 12):o3290. doi: 10.1107/S1600536810044028.
The title mol-ecule, C(21)H(26)O(3), has a six-membered planar carbon ring as the central core, substituted at position 1 with phen-oxy-carbonyl, at position 2 with hy-droxy and at positions 3 and 5 with tert-butyl groups. The structure shows two independent but very similar mol-ecules within the asymmetric unit. For both independent mol-ecules, the ester carboxyl-ate group is coplanar with the central core, as reflected by the small C-C-O-C torsion angles [179.95 (17) and 173.70 (17)°]. In contrast, the phenyl substituent is almost perpendicular to the carboxyl-ate -CO(2) fragment, as reflected by C-O-C-C torsion angles, ranging from 74 to 80°. The coplanarity between the central aromatic ring and the ester carboxyl-ate -CO(2)- group allows the formation of an intra-molecular hydrogen bond, with O⋯O distances of 2.563 (2) and 2.604 (2) Å.
3. tert-Butyl 3-(8-bromo-4H,10H-1,2-oxazolo[4,3-c][1]benzoxepin-10-yl)-2-methyl-1H-indole-1-carboxyl-ate
Ankur Trigunait, P Malathy, K Ramachandiran, P T Perumal, K Gunasekaran Acta Crystallogr Sect E Struct Rep Online. 2010 Jul 17;66(Pt 8):o2035. doi: 10.1107/S1600536810027297.
In the title compound, C(25)H(23)BrN(2)O(4), the seven-membered ring adopts a twisted-boat conformation. The indole ring system is planar within 0.021 (2) Å and the ester group [-C(=O)-O-C-] is almost coplanar with it [dihedral angle = 3.0 (2)°]. The conformation of the ester group is influenced by intra-molecular C-H⋯O inter-actions. In the crystal structure, mol-ecules are linked into chains along the b axis by C-H⋯N hydrogen bonds.
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