Fmoc-N-Me-3-(4-py)-L-Ala
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Fmoc-N-Me-3-(4-py)-L-Ala

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Fmoc-N-Me-3-(4-py)-L-Ala, a synthetic molecule, finds widespread use in the synthesis of peptides and proteins. Owing to its crucial role as a fundamental building block in solid-phase peptide synthesis, it has emerged as a potent weapon in the battle against numerous human maladies such as cancer and infectious diseases. With versatile functionality and chemical reactivity, the compound facilitates modifications and attachment to the peptide chain, rendering it a prized asset in the biomedical industry and a tool much sought after by researchers.

Category
Fmoc-Amino Acids
Catalog number
BAT-009000
CAS number
2381854-90-4
Molecular Formula
C24H22N2O4
Molecular Weight
402.4
Fmoc-N-Me-3-(4-py)-L-Ala
Size Price Stock Quantity
1 g $629 In stock
IUPAC Name
(2S)-2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]-3-pyridin-4-ylpropanoic acid
Synonyms
Fmoc-N(Me)4Pal-OH; (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-(pyridin-4-yl)propanoic acid
Density
1.3±0.1 g/cm3
Boiling Point
619.2±55.0 °C at 760 mmHg
InChI
InChI=1S/C24H22N2O4/c1-26(22(23(27)28)14-16-10-12-25-13-11-16)24(29)30-15-21-19-8-4-2-6-17(19)18-7-3-5-9-20(18)21/h2-13,21-22H,14-15H2,1H3,(H,27,28)/t22-/m0/s1
InChI Key
IZGNJWPYTSZXBJ-QFIPXVFZSA-N
Canonical SMILES
CN(C(CC1=CC=NC=C1)C(=O)O)C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Fmoc-N-Me-3-(4-py)-L-Ala, an amino acid derivative utilized in peptide synthesis, boasts diverse applications. Here are the key applications presented with a high degree of perplexity and burstiness:

Peptide Synthesis: At the forefront of solid-phase peptide synthesis, Fmoc-N-Me-3-(4-py)-L-Ala emerges as a pivotal player, enabling the integration of modified residues into peptide chains. This amino acid derivative imparts peptides with enhanced structural and functional attributes, elevating stability, bioavailability, and target specificity. Researchers wield this tool to craft peptides that stand resilient against enzymatic degradation, driving advancements in drug development and bioactivity enhancement.

Drug Development: Within the intricate realm of drug design, Fmoc-N-Me-3-(4-py)-L-Ala emerges as a linchpin, facilitating the creation of peptide-based drugs with augmented pharmacokinetic profiles. By incorporating this modified amino acid, researchers engineer peptides with heightened resistance to enzymatic breakdown, culminating in enhanced therapeutic effectiveness and prolonged longevity within biological systems. This modification heralds a new era of peptide drug development, steering towards improved patient outcomes and treatment regimens.

Structural Biology: Delving deep into the nuances of protein structure and function, Fmoc-N-Me-3-(4-py)-L-Ala assumes a critical role in unraveling the mysteries of protein folding dynamics. By introducing conformational constraints within peptides, researchers orchestrate a symphony of protein folding intricacies, shedding light on the delicate interplay between molecular structures and biological activities. This innovative approach fuels breakthroughs in structural biology, illuminating the intricacies of protein conformation and functionality.

Material Science: Pioneering the way in materials science, Fmoc-N-Me-3-(4-py)-L-Ala takes center stage in the synthesis of peptide-based hydrogels with far-reaching applications. These hydrogels find utility in diverse fields such as drug delivery, tissue engineering, and wound healing, thanks to the mechanical strength and customizable properties conferred by the incorporation of Fmoc-N-Me-3-(4-py)-L-Ala. This venture into material science innovation opens doors to novel solutions in regenerative medicine and biomaterial design, propelling the boundaries of interdisciplinary research and application.

1. Beta-turn-structure-assembled palladium complexes by complexation-induced self-organization of ferrocene-dipeptide conjugates
Toshiyuki Moriuchi, Takashi Fujiwara, Toshikazu Hirao Dalton Trans. 2009 Jun 14;(22):4286-8. doi: 10.1039/b817652c. Epub 2009 Jan 6.
A type II beta-turn-like structured ferrocene-dipeptide conjugate through intramolecular hydrogen bonding was formed by the introduction of only one minimum-sized peptide chain of the heterochiral sequence (-L-Ala-D-Pro-NH-4-Py or -D-Ala-L-Pro-NH-4-Py) into the ferrocene scaffold, which was subjected to a metal-directed assembly with [Pd(MeCN)(4)](BF(4))(2) to afford the beta-turn-structure-assembled palladium complex.
2. Syntheses and characterization of copper(II) carboxylate dimers formed from enantiopure ligands containing a strong π···π stacking synthon: enantioselective single-crystal to single-crystal gas/solid-mediated transformations
Daniel L Reger, Jacob J Horger, Agota Debreczeni, Mark D Smith Inorg Chem. 2011 Oct 17;50(20):10225-40. doi: 10.1021/ic201238n. Epub 2011 Sep 15.
Tri- and tetrafunctional enantiopure ligands have been prepared from 1,8-naphthalic anhydride and the amino acids L-alanine, D-phenylglycine, and L-asparagine to produce (S)-2-(1,8-naphthalimido)propanoic acid (HL(ala)), (R)-2-(1,8-naphthalimido)-2-phenylacetic acid (HL(phg)), and (S)-4-amino-2-(1,8 naphthalimido)-4-oxobutanoic acid (HL(asn)), respectively. Reactions of L(ala)(-) with copper(II) acetate under a variety of solvent conditions has led to the formation and characterization by X-ray crystallography of three similar copper(II) paddlewheel complexes with different axial ligands, [Cu(2)(L(ala))(4)(THF)(2)] (1), [Cu(2)(L(ala))(4)(HL(ala))] (2), and [Cu(2)(L(ala))(4)(py)(THF)] (3). A similar reaction using THF and L(phg)(-) leads to the formation of [Cu(2)(L(phg))(4)(THF)(2)] (4). With the exception of a disordered component in the structure of 4, the naphthalimide groups in all of these compounds are arranged on the same side of the square, central paddlewheel unit, forming what is known as the chiral crown configuration. A variety of π···π stacking interactions of the 1,8-naphthalimide groups organize all of these complexes into supramolecular structures. The addition of the amide group functionality in the L(asn)(-) ligand leads to the formation of tetrameric [Cu(4)(L(asn))(8)(py)(MeOH)] (5), where reciprocal axial coordination of one of the amide carbonyl oxygen atoms between two dimers leads to the tetramer. Extensive supramolecular interactions in 5, mainly the π···π stacking interactions of the 1,8-naphthalimide supramolecular synthon, support an open three-dimensional structure containing large pores filled with solvent. When crystals of [Cu(4)(L(asn))(8)(py)(MeOH)] are exposed to (S)-ethyl lactate vapor, the coordinated methanol molecule is replaced by (S)-ethyl lactate, bonding to the copper ion through the carbonyl oxygen, yielding [Cu(4)(L(asn))(8)(py)((S)-ethyl lactate)] (6) without a loss of crystallinity. With the exception of the replacement of the one axial ligand, the molecular structures of 5 and 6 are very similar. In a similar experiment of 5 with vapors of (R)-ethyl lactate, again a change occurs without a loss of crystallinity, but in this case the (R)-ethyl lactate displaces only slightly more than half of the axial methanol molecules forming [Cu(4)(L(asn))(8)(py){((R)-ethyl lactate)(0.58)(MeOH)(0.42)}] (7). Importantly, in 7, the (R)-ethyl lactate coordinates through the hydroxyl group. When crystals of [Cu(4)(L(asn))(8)(py)(MeOH)] are exposed to vapors of racemic ethyl lactate, the coordinated methanol molecule is displaced without a loss of crystallinity exclusively by (S)-ethyl lactate, yielding a new form of the tetramer [Cu(4)(L(asn))(8)(py)((S)-ethyl lactate)], in which the ethyl lactate in the pocket bonds to the copper(II) ion through the carbonyl oxygen as with 6. Exposure of [Cu(4)(L(asn))(8)(py){((R)-ethyl lactate)(0.58)(MeOH)(0.42)}] to racemic ethyl lactate yields a third form of [Cu(4)(L(asn))(8)(py)((S)-ethyl lactate)], where the three forms of [Cu(4)(L(asn))(8)(py)((S)-ethyl lactate)] have differences in the number of ordered (S)-ethyl lactate molecules located in the interstitial sites. These results demonstrate enantioselective bonding to a metal center in the chiral pocket of both 5 and 7 during single-crystal to single-crystal gas/solid-mediated exchange reactions.
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