82565-68-2

Basic information

• Product Name: Fmoc-L-4-Iodophenylalanine
• Synonyms: FMOC-L-4-IODOPHE;FMOC-L-4-IODOPHENYLALANINE;FMOC-PHE(4-I)-OH;FMOC-P-IODO-L-PHE-OH;FMOC-P-IODO-PHENYLALANINE;FMOC-P-IODO-PHE-OH;FMOC-PHE(P-I)-OH;FMOC-L-PHE(4-I)
• CAS NO: 82565-68-2
• Molecular Formula: C₂₄H₂₀INO₄
• Molecular Weight: 513.32
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Phenylalanine [Phe, F];Unusual Amino Acids;Fmoc-Amino acid series
• Mol File: 82565-68-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 213-217 °C(lit.)
• Boiling Point: 658.8oC at 760 mmHg
• Flash Point: 352.2oC
• Appearance: White powder
• Density: 1.577g/cm3
• Vapor Pressure: 2.97E-18mmHg at 25°C
• Refractive Index: 1.668
• Storage Temp.: 2-8°C
• PKA: 3.73±0.10(Predicted)
• Sensitive: Light Sensitive
• BRN: 4592723
• CAS DataBase Reference: Fmoc-L-4-Iodophenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-L-4-Iodophenylalanine(82565-68-2)
• EPA Substance Registry System: Fmoc-L-4-Iodophenylalanine(82565-68-2)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 8
• HazardClass: IRRITANT
• Hazardous Substances Data: 82565-68-2(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

Synthesis of a phosphotyrosine mimetic

InChI:InChI=1/C24H20INO4/c25-16-11-9-15(10-12-16)13-22(23(27)28)26-24(29)30-14-21-19-7-3-1-5-17(19)18-6-2-4-8-20(18)21/h1-12,21-22H,13-14H2,(H,26,29)(H,27,28)/t22-/m0/s1

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 62561-75-5 (R)-2-amino-3-(4-iodophenyl)propanoic acid 
• 1991-81-7 4-iodo-L-phenylalanine 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 

Downstream Products

• 114208-43-4 Fmoc-L-IPhe-OPfp 
• 300811-77-2 N-Fmoc-4-iodo-L-phenylalanine benzyl ester 
• 867335-92-0 [1-[(2,4-dimethoxy-benzyl)-prop-2-ynyl-carbamoyl]-2-(4-iodo-phenyl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 195258-67-4 (S)-methyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-iodophenyl)propanoate 
• 156017-45-7 (S)-2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}-3-{4-[(diethoxyphosphoryl)difluoromethyl]phenyl}propanoic acid 

Relevant articles and documents

Solid-phase synthesis of biaryl bicyclic peptides containing a 3-aryltyrosine or a 4-arylphenylalanine moiety

A methodology for the solid-phase synthesis of biaryl bicyclic peptides containing a Phe-Phe, a Phe-Tyr or a Tyr-Tyr motif has been devised. This approach comprises two key steps. The first one involves the cyclization of a linear peptidyl resin containing the corresponding halo- and boronoamino acids via a microwave-assisted Suzuki–Miyaura cross coupling. This step is followed by the macrolactamization of the resulting biaryl monocyclic peptidyl resin leading to the formation of the expected biaryl bicyclic peptide. This study provides the first solid-phase synthesis of this type of bicyclic compounds being amenable to prepare a diversity of synthetic or natural biaryl bicyclic peptides.

Synthesis and binding studies of two new macrocyclic receptors for the stereoselective recognition of dipeptides

We present here the design, synthesis, and analysis of a series of receptors for peptide ligands inspired by the hydrogen-bonding pattern of protein β-sheets. The receptors themselves can be regarded as strands 1 and 3 of a three-stranded β-sheet, with crosslinking between the chains through the 4-position of adjacent phenylalanine residues. We also report on the conformational equilibria of these receptors in solution as well as on their tendency to dimerize. 1H NMR titration experiments are used to quantify the dimerization constants, as well as the association constant values of the 1:1 complexes formed between the receptors and a series of diamides and dipeptides. The receptors show moderate levels of selectivity in the molecular recognition of the hydrogen-bonding pattern present in the diamide series, selecting the α-amino acid-related hydrogen-bonding functionality. Only one of the two cyclic receptors shows modest signs of enantioselectivity and moderate diastereoselectivity in the recognition of the enantiomers and diastereoisomers of the Ala-Ala dipeptide (DDG0 1 (DD-DL) = -1.08 kcal/mol and DDG0 1(DD-LD) = -0.89 kcal/mol). Surprisingly, the linear synthetic precursors show higher levels of stereoselectivity than their cyclic counterparts.

A concise synthesis of photoactivatable 4-aroyl-L-phenylalanines

An efficient preparation of the title compounds from 4-iodo-L-phenylalanines using a carbonylative Stille cross-coupling reaction as the key-step is described. (C) 2000 Elsevier Science Ltd. All rights reserved.