86060-82-4

Basic information

• Product Name: Nepsilon-Fmoc-Nalpha-Cbz-L-Lysine
• Synonyms: N-ALPHA-FMOC-N-EPSILON-Z-L-LYSINE;N-ALPHA-CARBOBENZOXY-N EPSILON-(9FLUORENYLMETHOXYCARBONYL)-L-LYSINE;N-ALPHA-FMOC-N-EPSILON-BENZYLOXYCARBONYL-L-LYSINE;N-(9-FLUORENYLMETHOXYCARBONYL)-N-EPSILON-CBZ-L-LYSINE;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-N-EPSILON-CARBOBENZOXY-L-LYSINE;N ALPHA-9-FLUORENYLMETHYLOXYCARBONYL-N OMEGA-BENZYLOXYCARBONYL-L-LYSINE;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-N-EPSILON-(BENZYL-OXYCARBONYL)-L-LYSINE;Z-LYSINE(FMOC)-OH
• CAS NO: 86060-82-4
• Molecular Formula: C₂₉H₃₀N₂O₆
• Molecular Weight: 502.56
• Product Categories: Amino Acid Derivatives;Lysine [Lys, K];Fmoc-Amino Acids and Derivatives;Fmoc-Amino acid series
• Mol File: 86060-82-4.mol

Chemical Properties

• Melting Point: 110-120 °C
• Boiling Point: 751.2 °C at 760 mmHg
• Flash Point: 408.1 °C
• Appearance: /
• Density: 1.261 g/cm³
• Vapor Pressure: 1.04E-23mmHg at 25°C
• Refractive Index: 1.603
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol
• PKA: 3.88±0.21(Predicted)
• BRN: 3578530
• CAS DataBase Reference: Nepsilon-Fmoc-Nalpha-Cbz-L-Lysine(CAS DataBase Reference)
• NIST Chemistry Reference: Nepsilon-Fmoc-Nalpha-Cbz-L-Lysine(86060-82-4)
• EPA Substance Registry System: Nepsilon-Fmoc-Nalpha-Cbz-L-Lysine(86060-82-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 86060-82-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Nepsilon-Fmoc-Nalpha-Cbz-L-Lysine is used as a building block in the synthesis of peptides and proteins for various pharmaceutical applications. Its protecting groups allow for the controlled stepwise assembly of complex peptide structures, which can be used as therapeutic agents, vaccines, or diagnostic tools.
Used in Chemical Synthesis:
In the field of chemical synthesis, Nepsilon-Fmoc-Nalpha-Cbz-L-Lysine serves as a versatile intermediate for the preparation of various L-Lysine derivatives. These derivatives can be used in the development of new drugs, agrochemicals, or other bioactive compounds.
Used in Research and Development:
Nepsilon-Fmoc-Nalpha-Cbz-L-Lysine is also used as a research tool in the study of protein structure, function, and interactions. Its unique protecting groups enable the synthesis of peptides with specific properties, which can be used to probe the mechanisms of protein folding, stability, and binding.
Used in Peptide Synthesis Education:
As a key component in peptide synthesis, Nepsilon-Fmoc-Nalpha-Cbz-L-Lysine is often used in educational settings to teach students the principles and techniques of peptide chemistry. This helps to develop a deeper understanding of the processes involved in the synthesis of biologically active peptides and proteins.

InChI:InChI=1/C29H30N2O6/c32-27(33)26(16-8-9-17-30-28(34)36-18-20-10-2-1-3-11-20)31-29(35)37-19-25-23-14-6-4-12-21(23)22-13-5-7-15-24(22)25/h1-7,10-15,25-26H,8-9,16-19H2,(H,30,34)(H,31,35)(H,32,33)/t26-/m0/s1

Upstream product

• 1155-64-2 N₆-[(benzyloxy)carbonyl]-L-lysine 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 88744-04-1 (9-fluorenyl)methyl pentafluorophenyl carbonate 

Downstream Products

• 86060-97-1 Fmoc-Lys(Z)-OPfp 
• 862473-40-3 Fmoc-L-Lys(Cbz)-Pro-OBu^t 
• 903518-34-3 cyclo-[Arg(Pbf)-Gly-Asp(OtBu)-D-Tyr(OtBu)-Lys-H] 
• 862473-27-6 (2S,2'S,3''S,4''S)-1-[2'-(3''-amino-2''-oxo-4''-vinyl-piperidin-1''-yl)-6'-benzyloxycarbonylamino-hexanoyl]-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 862473-26-5 (2S,2'S,3''S,4''S)-1-[6'-benzyloxycarbonylamino-2'-(3''-tert-butoxycarbonylamino-2''-oxo-4''-vinyl-piperidin-1''-yl)-hexanoyl]-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 862473-23-2 (4S,1'S,1'''S,2''''S)-4-(1'-{2''-[5'''-benzyloxycarbonylamino-1'''-(2''''-tert-butoxycarbonyl-pyrrolidine-1''''-carbonyl)-pentylamino]-ethyl}-allyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 862473-34-5 (2S,2'S,3''S,4''S,2'''S)-1-{2'-[3''-(2'''-amino-3'''-tert-butoxy-propionylamino)-2''-oxo-4''-vinyl-piperidin-1''-yl]-6'-benzyloxycarbonylamino-hexanoyl}-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 862473-29-8 (2S,2'S,3''S,4''S,2'''S)-1-{2'-[3''-(2'''-amino-3'''-benzyloxypropionylamino)-2''-oxo-4''-vinyl-piperidin-1''-yl]-6'-benzyloxycarbonylamino-hexanoyl}-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 862473-35-6 (2S,2'S,3''S,4''S,2'''S)-1-{2'-[3''-(2'''-acetylamino-3'''-tert-butoxy-propionylamino)-2''-oxo-4''-vinyl-piperidin-1''-yl]-6'-benzyloxycarbonylamino-hexanoyl}-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 862473-36-7 (3S,4R,2'S,1''S,2'''S)-3-(2'-acetylamino-3'-tert-butoxy-propionylamino)-1-[5''-benzyloxycarbonylamino-1''-(2'''-tert-butoxycarbonyl-pyrrolidine-1'''-carbonyl)-pentyl]-2-oxo-piperidine-4-carboxylic acid 
• 862473-30-1 (2S,2'S,3''S,4''S,2'''S)-1-{2'-[3''-(2'''-acetylamino-3'''-benzyloxy-propionylamino)-2''-oxo-4''-vinyl-piperidin-1''-yl]-6'-benzyloxycarbonylamino-hexanoyl}-pyrrolidine-2-carboxylic acid tert-butyl ester 

Relevant articles and documents

Synthesis method of double different protected amino acids

The invention relates to a synthesis method of double different protected amino acids.The technical problems of harsh reaction conditions, inapplicability of production enlarging and the like in an existing synthesis method are mainly solved. According to the technical scheme, the synthesis method of double different protected amino acids comprises the following steps: one of Boc20, Alloc-Cl or Cbz-Osuis added to amino alcohol under the action of an alkaline reagent to obtain a compound 1; the compound 1 reacts with methanesulfonyl chloride or paratoluensulfonyl chloride to obtain an intermediate, then a halide is added into acetone, heating and refluxing are executed to obtain a compound 2; the compound 2 is condensed with diethyl acetamidomalonate under the action of an alkaline agent togenerate a compound 3; the compound 3 is dissolved in alcohol and water, an inorganic base is added, heating, hydrolyzing and decarboxylating are executed to obtain a compound 4; acetylase is added into deionized water to obtain a compound 5 through enzymolysis; amino acid protection is executed, wherein one of Fmoc-Osu, Cbz-OSu, Alloc-Cl or Boc20 is added into thecompound 5 under the action of an alkaline agent to generatea target compound A.

Structure-based design of pseudopeptidic inhibitors for SIRT1 and SIRT2

The lack of substrate-bound crystal structures of SIRT1 and SIRT2 complicates the drug design for these targets. In this work, we aim to study whether SIRT3 could serve as a target structure in the design of substrate based pseudopeptidic inhibitors of SIRT1 and SIRT2. We created a binding hypothesis for pseudopeptidic inhibitors, synthesized a series of inhibitors, and studied how well the fulfillment of the binding criteria proposed by the hypothesis correlated with the in vitro inhibitory activities. The chosen approach was further validated by studying docking results between 12 different SIRT3, Sir2Tm, SIRT1 and SIRT2 X-ray structures and homology models in different conformational forms. It was concluded that the created binding hypothesis can be used in the design of the substrate based inhibitors of SIRT1 and SIRT2 although there are some reservations, and it is better to use the substrate-bound structure of SIRT3 instead of the available apo-SIRT2 as the target structure.

Nε-Modified lysine containing inhibitors for SIRT1 and SIRT2

Sirtuins catalyze the NAD+ dependent deacetylation of N ε-acetyl lysine residues to nicotinamide, O′-acetyl-ADP- ribose (OAADPR) and Nε-deacetylated lysine. Here, an easy-to-synthesize Ac-Ala-Lys-Ala sequence has been used as a probe for the screening of novel Nε-modified lysine containing inhibitors against SIRT1 and SIRT2. Nε-Selenoacetyl and N ε-isothiovaleryl were the most potent moieties found in this study, comparable to the widely studied Nε-thioacetyl group. The Nε-3,3-dimethylacryl and Nε-isovaleryl moieties gave significant inhibition in comparison to the Nε-acetyl group present in the substrates. In addition, the studied Nε- alkanoyl, Nε-α,β-unsaturated carbonyl and N ε-aroyl moieties showed that the acetyl binding pocket can accept rather large groups, but is sensitive to even small changes in electronic and steric properties of the Nε-modification. These results are applicable for further screening of Nε-acetyl analogues.

Mild, selective cleavage of amino acid and peptide β-(trimethylsilyl)ethoxymethyl (SEM) esters by magnesium bromide

Magnesium bromide etherate has been previously shown to cleave β-(trimethylsilyl)ethoxymethyl (SEM) esters of aliphatic acids. This methodology has now been extended to amino acid and peptide derivatives in the presence of protecting groups typically encountered in peptide chemistry, including the Boc, Cbz, Fmoc and Troc carbamates as well as benzyl-, tert-butyl- and tert-butyldimethylsilyl ethers. The stability of fluoride sensitive protecting groups to magnesium bromide allows for added selectivity in the removal of SEM esters in organic synthesis.

Angiopeptin cyclopeptide compounds

The invention relates to a compound selected from those of formula (I) (SEQ ID NO:1): STR1 in which R1, R2, X1 and X2 are as defined in the description, useful as inhibitor of the proliferation component of vascular smooth muscle cells.

Selective deprotection of phenacyl, benzyl and methyl esters of N-protected amino acids and dipeptides and N-protected amino acids benzyl ester linked to resins with bis(tributyltin) oxide

Phenacyl, methyl and benzyl esters of various N-α-Boc, N-α-Cbz or N,N-dimethylamino protected amino acids and dipeptides, as well as esters of N-α-protected amino acids linked to Wang and Pam resins have been efficiently and chemoselectively cleaved by bis(tributyltin) oxide in aprotic solvents to give the corresponding carboxylic acids in good yields. Moreover, the absence of racemization during the deprotection has been demonstrated. A limitation of the method is the instability of the N-ε-Fmoc group in the amino acid esters 8 and 10, N-α-Fmoc-L-alanine linked to Wang resin 23 and the Cbz protecting groups in N-α-Boc-N-ε-Cbz-L-lysine benzyl and methyl esters (5 and 7), respectively, and N-α-Cbz-L-alanyl-L-alanine methyl ester 19. In the case of N-α-protected dipeptides, there was no evidence of free amino acid which indicates that the peptide bond is unaffected.

Nε-carbonyl> Derivatives of Tri-L-lysine and Tetra-L-lysine as Potential Intermediates in the Block Polymer Synthesis of Macromolecular Drug Conjugates

Tri-L-lysine and tetra-L-lysine derivatives were synthesized with Nε-carbonyl>(Nε-Teoc) protecting groups an all the lysines, or on all but the N-terminal lysine, and with Nα-(tert-butyloxycarbonyl) (Nα-Boc) or Nα-(9-fluorenylmethyloxycarbonyl) (Nα-Fmoc) groups on the N-terminal lysines.Treatment of the Boc/Teoc peptides with p-toluenesulfonic or 2,4,6-trimethylbenzenesulfonic acid led to Boc cleavage with Teoc retention only when the Teoc/Boc ratio was 1:1 or 2:1.In contrast, treatment of the Fmoc/Teoc peptides with liquid ammonia in a sealed vessel cleaved the Fmoc group without significant loss of Teoc groups even when the Fmoc/Teoc ratio was 3:1, showing that Fmoc and Teoc groups provide more selectivity than the Boc and Teoc combination.Nα-Fmoc and Nε-Teoc groups were both stable under catalytic hydrogenolysis conditions.This made it possible to prepare Nα-Fmoc-tri-L-lysine and Nα-Fmoc-tetra-L-lysine derivatives with Nε-Teoc groups on all but the N-terminal lysine and demonstrated that the triad Fmoc/Cbz/Teoc is superior to Boc/Cbz/Teoc in peptide synthesis involving the orthogonal protection strategy.

Process for the preparation of pentapeptides having an action on the immune system and intermediate products for this process

The invention relates to a process for the preparation of peptides of the general formula in which S denotes glutamic acid or α-aminoadipic acid and Y denotes tyrosine or tryptophan or esters or amides thereof, which comprises subjecting tetrapeptides of the formula in which Z' represents a protective group of the benzyl type, to a condensation reaction with corresponding tyrosine esters or amides or tryptophan esters or amides and removing the protective groups by hydrogenation. The invention furthermore relates to tetrapeptides as intermediate products of this process.

9-Fluorenylmethyl Pentafluorophenyl Carbonate as a Useful Reagent for the Preparation of N-9-Fluorenylmethyloxycarbonylamino Acids and their Pentafluorophenyl Esters

9-Fluorenylmethyl pentafluorophenyl carbonate is a useful reagent for the efficient, side reaction-free introduction of N-9-fluorenylmethyloxycarbonyl protecting group into amino acids and for the subsequent preparation of their pentafluorophenyl esters.Some new compounds of both types are described.

Solid Phase Synthesis of Substance P and Its Analogues Employing 9-Fluorenylmethoxycarbonylamino Acid Active Esters

Substance P and six of its analogues containing D-p-hydroxyphenylglycine at positions 7 and/or 8 have been synthesized employing fluorenylmethoxycarbonylamino acid (Fmoc) active esters and p-alkoxybenzyl alcohol resin.Diethylamine is employed for the cleavage of Fmoc-group.The agonistic and antagonistic activities of the peptides have been studied.