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tBuO-Ste-Glu(AEEA-AEEA-OH)-OtBu

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tBuO-Ste-Glu(AEEA-AEEA-OH)-OtBu Basic information

Product Name:
tBuO-Ste-Glu(AEEA-AEEA-OH)-OtBu
Synonyms:
  • (S)-22-(Tert-butoxycarbonyl)-10,19,24-trioxo-3,6,12,15-tetraoxa-9,18,23-triazahentetracontane-1,41-dioic acid
  • Octadecane(OtBu)-Glu(ɑ-OtBu)-AEEA-AEEA-OH
  • Side chain
  • tBuO-Ste-Glu(AEEA-AEEA-OH)-OtBu
  • Semaglutide side chain
  • Fmoc-L-Lys[OctotBu)-Glu-(otBu)-AEEA-AEEA]-OHu
  • (S)-22-(tert-butoxycarbonyl)-43,43-dimethyl-10,19,24,41-tetraoxo-3,6,12,15,42-pentaoxa-9,18,23-triazatetratetracontanoic acid
  • Egf(a) analogue-13C4
CAS:
1118767-16-0
MF:
C43H79N3O13
MW:
846.1
Mol File:
1118767-16-0.mol
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tBuO-Ste-Glu(AEEA-AEEA-OH)-OtBu Chemical Properties

Boiling point:
940.6±65.0 °C(Predicted)
Density 
1.079±0.06 g/cm3(Predicted)
storage temp. 
Keep in dark place, Sealed in dry, Store in freezer, under -20°C
solubility 
Ethanol: Slightly soluble: 0.1-1 mg/ml
form 
Solid
pka
3.39±0.10(Predicted)
color 
White to off-white
InChIKey
YZUXNRZPWYRMGH-DHUJRADRSA-N
SMILES
C(O)(=O)COCCOCCNC(=O)COCCOCCNC(=O)CC[C@@H](C(OC(C)(C)C)=O)NC(=O)CCCCCCCCCCCCCCCCC(OC(C)(C)C)=O
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tBuO-Ste-Glu(AEEA-AEEA-OH)-OtBu Usage And Synthesis

Description

tBuO-Ste-Glu(AEEA-AEEA-OH)-OtBu is the 18-carbon fatty acid side chain of somatostatin, which contributes to an increased affinity for albumin (approximately 5-6 fold). Somalutide is a glucagon-like peptide-1 (GLP-1) analogue with hypoglycaemic properties.

Uses

(S)-22-(Tert-butoxycarbonyl)-10,19,24-trioxo-3,6,12,15-tetraoxa-9,18,23-triazahentetracontane-1,41-dioic acid can be used as an intermediate in organic synthesis, mainly used in laboratory research and development and chemical production processes.

Definition

TBuO-Ste-Glu(AEEA-AEEA-OH)-OtBu is also known as Semaglutide Side Chain. An 18-carbon fatty acid side chain of semaglutide. The affinity of the semaglutide side chain for albumin was enhanced 5-6 times. Semaglutide is a glucagon-like peptide-1 (GLP-1) analog with significant hypoglycemic efficacy.

Application

OLED intermediates, Pharmaceutical Raw Intermediates, Fine Chemical Intermediate

References

[1] IVAN GURYANOV*. Copper(II) Lysinate and Pseudoproline Assistance in the Convergent Synthesis of the GLP-1 Receptor Agonists Liraglutide and Semaglutide[J]. Organic Process Research & Development, 2021, 25 7: 1598-1611. DOI: 10.1021/acs.oprd.1c00021
[2] THOMAS B. KJELDSEN. Engineering of Orally Available, Ultralong-Acting Insulin Analogues: Discovery of OI338 and OI320[J]. Journal of Medicinal Chemistry, 2020, 64 1: 616-628. DOI: 10.1021/acs.jmedchem.0c01576

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