CAS 132388-59-1 Fmoc-Asn(Trt)-OH (HCID 640248)

Names & identifiers

Preferred name: Fmoc-Asn(Trt)-OH
IUPAC: (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxo-4-(tritylamino)butanoic acid
English name: Fmoc-Asn(Trt)-OH
Molecular formula: C38H32N2O5
Molecular weight: 596.67

Names & synonyms

Fmoc-Asn(Trt)-OH132388-59-1DTXSID80348710N2-[(9H-Fluoren-9-ylmethoxy)carbonyl]-N-(triphenylmethyl)-L-asparagineN2-((9H-Fluoren-9-ylmethoxy)carbonyl)-N-(triphenylmethyl)-L-asparagineRefChem:599518DTXCID70299782603-578-8Nalpha-Fmoc-Ngamma-trityl-L-asparagineMFCD00077049(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxo-4-(tritylamino)butanoic acid(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-oxo-4-(tritylamino)butanoic acid

Show more names

FMOC-ASN(TRT)FMOC-L-ASN(TRT)-OHFMOC-N-TRITYL-L-ASPARAGINENα-Fmoc-Nγ-trityl-L-asparagineL-Asn(Trt)FMoc-Asn(Tre)

SCHEMBL118112Nalpha-[(9H-Fluoren-9-ylmethoxy)carbonyl]-Ngamma-trityl-L-asparagineM03352AKOS015924190CS-W002327N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N4-trityl-L-asparagine(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-[(triphenylmethyl)carbamoyl]propanoic acidC38H32N2O5

Database identifiers

CAS: 132388-59-1
PubChem CID: 640248
DTXSID: DTXSID80348710
UNII: 5R94765WYL
EC Number: 603-578-8
Nikkaji: J956.314H

Properties

Computed structural properties

XLogP: 6.6
Topological polar surface area: 105 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 5
Rotatable bonds: 11
Heavy atoms: 45
Formal charge: 0
Complexity: 931

Physicochemical properties

Melting point: 201 · 201-204 °C(lit.)
Boiling point: 858.1 · 858.1±65.0 °C(Predicted)
alpha: -16 · -16 º (c=1, MeOH)
Density: 1.271 · 1.271±0.06 g/cm3(Predicted)
refractive index: -19 ° · -19 ° (C=1, DMF)
storage temp.: 2 · 2-8°C
solubility: 0.00005 g/l · <0.00005g/l
pka: 3.79 · 3.79±0.10(Predicted)
form: powder to crystal
color: White to Almost white
optical activity: 20 · [α]20/D 15.0±1°, c = 1% in methanol
Water Solubility: 0.00005 g/L · <0.00005g/L
BRN: 4343823 · 4343823
Major Application: peptide synthesis
InChIKey: KJYAFJQCGPUXJY-UUWRZZSWSA-N
SMILES: C(O)(=O)[C@H](CC(N)=O)N(C(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
CAS DataBase Reference: 132388 · 132388-59-1(CAS DataBase Reference)
FDA UNII: 5 R94765WYL · 5R94765WYL
UNSPSC Code: 12352209 · 12352209
NACRES: 26 · NA.26
Symbol(GHS): 9 · GHS09
Signal word: Warning
Hazard statements: 411 · H411
Precautionary statements: 273 · P273-P391-P501
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Risk Statements: 53 · 53
Safety Statements: 24 · 24/25-61
RIDADR: 3077 · UN 3077 9 / PGIII
WGK Germany: 2 · 2
F: 3 · 3-10
HS Code: 2924 · 2924 29 70
HazardClass: IRRITANT
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 · Aquatic Chronic 2
Toxicity: 50 orally · LD50 orally in Rabbit: > 2000 mg/kg

Safety & regulation

GHS classification

GHS Classification · 4 items

This chemical does not meet GHS hazard criteria for 2% (1 of 50) of reports.

H413 (92%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]

P273, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 50 reports by companies from 7 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAquatic Chronic 4 (92%)

Safety data

F: 3-10
PPE: Eyeshields, Gloves, type N95 (US)
wgk: 2
ridadr: UN 3077 9 / PGIII
hs_code: 2924 29 70
Toxicity: LD50 orally in Rabbit: > 2000 mg/kg
risk_code: 53
Signal word: Warning
Symbol(GHS): GHS09
safety_code: 24/25-61
hazard_class: IRRITANT
Storage Class: 11 - Combustible Solids
Hazard statements: H411
Hazard Classifications: Aquatic Chronic 2
Precautionary statements: P273-P391-P501

Chemistry & industry

Applications · 2 items

DescriptionFmoc-Asn(Trt)-OH prevents the possibility of the amide side chain from undergoing dehydration side reactions during activation, especially with carbodiimide reagents. Fmoc-Asn(Trt)-OH dissolves readily in all standard peptide synthesis reagents, while Fmoc-Asn-OH is only somewhat soluble in NMP or DMF. The trityl group is removed with TFA. This reaction is usually complete within 1 hour at room temperature, but is slower when the Asn(Trt) residue in at the N-terminal of the peptide. In these cases, the deprotection reaction should be extended to 2 hours.

UsesFmoc-Asn(Trt)-OH, is an amino acid derivative used in chemical synthesis and peptide chemistry.

Preparation methods · 1 item

PreparationSynthesis of Fmoc-Asn(Trt)-OH:Step 1: Crystallization to form N'-Trityl-L-asparagine crystals.Step 2: Centrifugation to extract N'-Trityl-L-asparagine crystals.Step 3: Washing to remove residual starting materials in the synthesis.Step 4: Extraction to obtain N-Acetyl-L-asparagine.Step 5: Centrifugation to extract N'-Trityl-L-asparagine.Step 6: Drying to obtain the final product.This synthesis method effectively removes residual synthetic materials such as trifluoroacetic acid, maleic anhydride, and epichlorohydrin, which are similar in chemical properties to N-Acetyl-L-asparagine, from the product during the production process. The purification method is simple and the product obtained has high purity.