87420-41-5

Usage

Uses

Used in Biochemistry and Cell Biology Research:
N-ALPHA-PALMITOYL-S-[2,3-BIS(PALMITOYLOXY)-(2RS)-PROPYL]-L-CYSTEINE is used as a research tool for studying protein palmitoylation, a post-translational modification that influences protein localization, function, and interactions with lipid membranes. It aids in understanding the role of this modification in various cellular processes.
Used in the Study of Lipid-Protein Interactions:
In the field of lipid-protein interactions, N-ALPHA-PALMITOYL-S-[2,3-BIS(PALMITOYLOXY)-(2RS)-PROPYL]-L-CYSTEINE is utilized as a reagent to explore how proteins interact with lipids, which is essential for many cellular functions, including signal transduction and membrane dynamics.
Used in Investigating Cell Signaling:
N-ALPHA-PALMITOYL-S-[2,3-BIS(PALMITOYLOXY)-(2RS)-PROPYL]-L-CYSTEINE is used as a research compound to delve into the mechanisms of cell signaling, where protein palmitoylation can modulate the activity and localization of signaling molecules, impacting cellular responses.
Used in Membrane Trafficking Research:
N-ALPHA-PALMITOYL-S-[2,3-BIS(PALMITOYLOXY)-(2RS)-PROPYL]-L-CYSTEINE is also used in the study of membrane trafficking, where protein palmitoylation plays a role in the sorting, targeting, and fusion of membrane-bound vesicles within the cell.
Used in Pharmaceutical Development:
Although not explicitly mentioned in the provided materials, due to its role in cell biology and potential effects on protein function, N-ALPHA-PALMITOYL-S-[2,3-BIS(PALMITOYLOXY)-(2RS)-PROPYL]-L-CYSTEINE could potentially be used in the development of pharmaceuticals targeting diseases related to protein palmitoylation dysregulation.
Used in the Development of Drug Delivery Systems:
Given its interaction with cell membranes, N-ALPHA-PALMITOYL-S-[2,3-BIS(PALMITOYLOXY)-(2RS)-PROPYL]-L-CYSTEINE could be explored for use in the design of drug delivery systems that require specific targeting or cellular uptake mechanisms.

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

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

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