87420-41-5

Basic information

• Product Name: N-ALPHA-PALMITOYL-S-[2,3-BIS(PALMITOYLOXY)-(2RS)-PROPYL]-L-CYSTEINE
• Synonyms: PALMITOYL-CYS((RS)-2,3-DI(PALMITOYLOXY)-PROPYL)-OH;PALMITOYL-S-[2,3-BIS(PALMITOYLOXY)-(2RS)-PROPYL]-L-CYSTEINE;PALMITOYL-CYSTEINE((RS)-2,3-DI(PALMITOYLOXY)-PROPYL)-OH;PAM3CYS-OH;PAM-CYS[(2,3-BIS-PAMO)PR]-OH;N-ALPHA-PALMITOYL-S-[2,3-BIS(PALMITOYLOXY)-(2RS)-PROPYL]-L-CYSTEINE;2,3-bis(palmitoyloxy)-2-propyl-1-palmitoylcysteine;Palmitoyl-Cys((RS)-2,3-di(palmitoyloxy)-propyl)-OH, N-α-Palmitoyl-S-[2,3-bis(palmitoyloxy)-(2RS)-propyl]-L-cysteine
• CAS NO: 87420-41-5
• Molecular Formula: C₅₄H₁₀₃NO₇S
• Molecular Weight: 910.46
• Mol File: 87420-41-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 907.8°C at 760 mmHg
• Flash Point: 502.8°C
• Appearance: /
• Density: 0.966g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.482
• Storage Temp.: -15°C
• PKA: 3.28±0.10(Predicted)
• CAS DataBase Reference: N-ALPHA-PALMITOYL-S-[2,3-BIS(PALMITOYLOXY)-(2RS)-PROPYL]-L-CYSTEINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-ALPHA-PALMITOYL-S-[2,3-BIS(PALMITOYLOXY)-(2RS)-PROPYL]-L-CYSTEINE(87420-41-5)
• EPA Substance Registry System: N-ALPHA-PALMITOYL-S-[2,3-BIS(PALMITOYLOXY)-(2RS)-PROPYL]-L-CYSTEINE(87420-41-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 87420-41-5(Hazardous Substances Data)

Usage

General Description

N-ALPHA-PALMITOYL-S-[2,3-BIS(PALMITOYLOXY)-(2RS)-PROPYL]-L-CYSTEINE is a synthetic compound used in the field of biochemistry and cell biology. It is a palmitoylated derivative of the amino acid cysteine, and is often used as a tool for studying protein palmitoylation and lipid-protein interactions. This chemical is known to be an effective palmitoylation reagent, mediating the lipidation of proteins and promoting their interaction with cell membranes. N-ALPHA-PALMITOYL-S-[2,3-BIS(PALMITOYLOXY)-(2RS)-PROPYL]-L-CYSTEINE is also used in research related to the role of protein palmitoylation in cell signaling, membrane trafficking, and other cellular processes.

InChI:InChI=1/C54H103NO7S/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-51(56)55-50(54(59)60)48-63-47-49(62-53(58)45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)46-61-52(57)44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h49-50H,4-48H2,1-3H3,(H,55,56)(H,59,60)/t49?,50-/m0/s1

Synthetic route

3-((R)-3-(allyloxy)-3-oxo-2-palmitamidopropylthio)propane-1,2-diyl dipalmitate (1610431-29-2) → S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine (87420-41-5)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); N-methylaniline In tetrahydrofuran at 20℃; for 1h;	97%
With tetrakis(triphenylphosphine) palladium(0); N-methylaniline In tetrahydrofuran at 20℃; for 1h;	97%

(R)-allyl 2-(tert-butoxycarbonylamino)-3-((2,2-dimethyl-1,3-dioxolan-4-yl)methylthio)propanoate (1610431-05-4) → S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine (87420-41-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: acetic acid / 20 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 20 °C / Cooling with ice 3: trifluoroacetic acid / dichloromethane / 20 °C 4: 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 5: tetrakis(triphenylphosphine) palladium(0); N-methylaniline / tetrahydrofuran / 1 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1: acetic acid / 20 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 20 °C / Cooling with ice 3: trifluoroacetic acid / dichloromethane / 20 °C 4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 5: tetrakis(triphenylphosphine) palladium(0); N-methylaniline / tetrahydrofuran / 1 h / 20 °C View Scheme

(R)-allyl 2-(tert-butoxycarbonylamino)-3-(2,3-dihydroxypropylthio)propanoate (1610431-06-5) → S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine (87420-41-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 20 °C / Cooling with ice 2: trifluoroacetic acid / dichloromethane / 20 °C 3: 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 4: tetrakis(triphenylphosphine) palladium(0); N-methylaniline / tetrahydrofuran / 1 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 20 °C / Cooling with ice 2: trifluoroacetic acid / dichloromethane / 20 °C 3: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 4: tetrakis(triphenylphosphine) palladium(0); N-methylaniline / tetrahydrofuran / 1 h / 20 °C View Scheme

3-((R)-3-(allyloxy)-2-amino-3-oxopropylthio)propane-1,2-diyl dipalmitate (1610431-28-1) + 1-hexadecylcarboxylic acid (57-10-3) → S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine (87420-41-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: tetrakis(triphenylphosphine) palladium(0); N-methylaniline / tetrahydrofuran / 1 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: tetrakis(triphenylphosphine) palladium(0); N-methylaniline / tetrahydrofuran / 1 h / 20 °C View Scheme

(2R)-3-(3-(allyloxy)-2-(tert-butoxycarbonylamino)-3-oxopropylthio)propane-1,2-diyl dipalmitate (1610431-07-6) → S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine (87420-41-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: trifluoroacetic acid / dichloromethane / 20 °C 2: 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 3: tetrakis(triphenylphosphine) palladium(0); N-methylaniline / tetrahydrofuran / 1 h / 20 °C View Scheme

(R)-3-(3-(allyloxy)-2-(tert-butoxycarbonylamino)-3-oxopropylthio)propane-1,2-diyl dipalmitate → S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine (87420-41-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: trifluoroacetic acid / dichloromethane / 20 °C 2: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 3: tetrakis(triphenylphosphine) palladium(0); N-methylaniline / tetrahydrofuran / 1 h / 20 °C View Scheme

S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine (87420-41-5) + 6-(amino)hexyl (α-D-mannopyranosyl)-(1->2)-O-(α-D-mannopyranosyl)-(1->2)-O-[(β-D-galactopyranosyl)-(1->4)]-α-D-mannopyranoside (351011-55-7) → 6-(N-palmitoyl-S-[2,3-bis(palmitoyloxy)-(2R,2S)-propyl]-L-cystenyl)hexyl-(α-D-mannopyranosyl)-(1->2)-O-(α-D-mannopyranosyl)-(1->2)-O-[(β-D-galactopyranosyl)-(1->4)]-α-D-mannopyranoside

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane; N,N-dimethyl-formamide at 20℃; for 20h;	60%

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Val-OH (68858-20-8) + Fmoc-Leu-OH (35661-60-0) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3) + N-Fmoc L-Phe (35661-40-6) + Fmoc-Ser(tBu)-OH (71989-33-8) + Fmoc-(tBu)Asp-OH (71989-14-5) + Fmoc-Glu(OtBu)-OH (71989-18-9) + Fmoc-Ile-OH (71989-23-6) + Fmoc-Lys(tert-butoxycarbonyl) (71989-26-9) + L-Asn(Trt) (132388-59-1) + Fmoc-L-Gln(Trt)-OH (132327-80-1) + S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine (87420-41-5) + Fmoc-Lys(Mmt)-OH (159857-60-0) → palmitoyl-Cys((RS)-2,3-di(palmitoyloxy)propyl)-Ser-Lys-Lys-Lys-Lys-Asp-Glu-Val-Ser-Gly-Leu-Glu-Gln-Leu-Glu-Ser-Ile-Ile-Asn-Phe-Glu-Lys-Leu-Ala-Ala-Ala-Ala-Ala-Lys-NH2

Conditions

Yield

Stage #1: Fmoc-Lys(Mmt)-OH With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V) In N,N-dimethyl-formamide Stage #2: With piperidine In N,N-dimethyl-formamide Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Val-OH; Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; N-Fmoc L-Phe; Fmoc-Ser(tBu)-OH; Fmoc-(tBu)Asp-OH; Fmoc-Glu(OtBu)-OH; Fmoc-Ile-OH; Fmoc-Lys(tert-butoxycarbonyl); L-Asn(Trt); Fmoc-L-Gln(Trt)-OH; S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine Further stages;

5%

...Expand

H-Asn-Ser(But)-Gly-Gly-Ser(But)-OBut (134982-15-3) + S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine (87420-41-5) → S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-Cys-Asn-Ser(But)-Gly-Gly-Ser(But)-OBut (142292-21-5)

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide 1) DMF, CH2Cl2, 30 min, ice-salt cooling 2) CH2Cl2, 15 h, r.t.; Yield given. Multistep reaction;

C108H153N14O19PolS2 + S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine (87420-41-5) → N-palmitoyl-S-[2,3-bis(palmitoyloxy)-(2RS)-propyl]-[R]-cysteinyl-[S]-seryl-[S]-lysyl-[S]-lysyl-[S]-lysyl-[S]-lysine-[R]-cysteinyl-[S]-lysyl-biotin

Conditions

Yield

Stage #1: S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine With 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide for 0.333333h; Stage #2: C108H153N14O19PolS2 In dichloromethane; N,N-dimethyl-formamide at 20℃; for 20h; Stage #3: With chlorotriisopropylsilane; trifluoroacetic acid In dichloromethane; water; N,N-dimethyl-formamide for 3h;

7.3 mg

PS-carbodiimide + S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine (87420-41-5) + tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate (153086-78-3) → N-Pam3Cys-(N'-Boc-2,2'-(ethylenedioxy)diethylamine)

Conditions	Yield
Stage #1: PS-carbodiimide; S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine With PS-carbodiimide resin In dichloromethane for 0.0833333h; Inert atmosphere; Stage #2: tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate In dichloromethane for 16h;

Upstream product

• 1610431-05-4 (R)-allyl 2-(tert-butoxycarbonylamino)-3-((2,2-dimethyl-1,3-dioxolan-4-yl)methylthio)propanoate 
• 1610431-06-5 (R)-allyl 2-(tert-butoxycarbonylamino)-3-(2,3-dihydroxypropylthio)propanoate 
• 1610431-28-1 3-((R)-3-(allyloxy)-2-amino-3-oxopropylthio)propane-1,2-diyl dipalmitate 
• 57-10-3 1-hexadecylcarboxylic acid 
• 1610431-07-6 (2R)-3-(3-(allyloxy)-2-(tert-butoxycarbonylamino)-3-oxopropylthio)propane-1,2-diyl dipalmitate 
• 1610431-29-2 3-((R)-3-(allyloxy)-3-oxo-2-palmitamidopropylthio)propane-1,2-diyl dipalmitate 

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