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Application Area

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

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category

Fmoc-Amino Acids

Catalog number

BAT-009009

Molecular Formula

C22H24INO4

Molecular Weight

493.33

IUPAC Name

tert-butyl (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-iodopropanoate

Synonyms

(S)-tert-Butyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-iodopropanoate; tert-butyl (2S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-iodopropanoate

N-Fmoc-3-iodo-D-alanine tert-butyl ester, a specialized chemical reagent utilized in organic synthesis and biochemical research, boasts diverse applications in various fields. Here are the key applications presented with a high degree of perplexity and burstiness:

Peptide Synthesis: A cornerstone in solid-phase peptide synthesis, N-Fmoc-3-iodo-D-alanine tert-butyl ester plays a pivotal role in embedding the 3-iodo-D-alanine residue into burgeoning peptide chains. This reagent is instrumental in concocting customized peptides with distinct characteristics crucial in the realms of drug development and protein engineering.

Chemical Biology: Within the domain of chemical biology, this compound acts as a vital building block for crafting intricate molecules tailored to delve into biological systems. The iodine atom within the alanine residue offers avenues for further derivatization or the introduction of radioactive isotopes for tracing studies. Such applications are invaluable in dissecting protein interactions and cellular processes.

Medicinal Chemistry: Renowned in the hands of medicinal chemists, N-Fmoc-3-iodo-D-alanine tert-butyl ester is a linchpin in the creation of novel pharmaceutical compounds. Its innate ability for selective modification renders it indispensable in synthesizing drugs with heightened efficacy and diminished side effects. This compound facilitates the generation of analogs ripe for screening therapeutic activity, offering profound insights into the realm of drug design.

Structure-Activity Relationship Studies: Researchers harness the powers of N-Fmoc-3-iodo-D-alanine tert-butyl ester to scrutinize the structure-activity relationships of peptides and proteins. Through methodically altering the position of 3-iodo-D-alanine, scientists pinpoint pivotal structural characteristics crucial for biological activity. These studies play a pivotal role in fine-tuning bioactive compounds and unraveling their mechanisms of action, paving the way for groundbreaking advancements in the field.

1. 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.

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. 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.