oxyma-b, an excellent racemization suppressor in peptide ... · supporting information oxyma-b, an...
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Supporting Information
Oxyma-B, an Excellent Racemization Suppressor in Peptide
Synthesis
Yahya E. Jad,aSherine N. Khattab,
b Beatriz G. de la Torre,
a,cThavendran Govender,
aHendrik G.
Kruger,aAyman El-Faham
b,d,* and Fernando Albericio
a,c,e,f,g*
a aCatalysis and Peptide Research Unit, School of Health Sciences, University ofKwazulu-Natal, Durban 4001, South Africa. E-mail:
[email protected] bDepartment of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, Egypt. E-mail:
[email protected] cSchool of Chemistry, Yachat Tech, Yachay City of Knowledge, 100119-Urcuqui, Ecuador d Department of Chemistry, College of Science, King Saud University, P.O. Box 2455,Riyadh11451, Saudi Arabia eSchool of Chemistry and Physics, University of KwaZulu-Natal, Durban 4001, South Africa
fInstitute for Research in Biomedicine and CIBER-BBN, Barcelona 08028, Spain
gDepartment of Organic Chemistry, University of Barcelona, Barcelona 08028, Spain
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2014
1H NMR of Oxyma-B in CDCl3
13C NMR of Oxyma-B in acetonitrile-d4
HPLCs
1- Z-Phg-Pro-NH2 Racemization test:
1.1- HOBt
1.2-HOAt
1.3-OxymaPure
1.4-Oxyma-B
2-Z-Phe-Val-Pro-NH2 Racemization test:
2.1- HOBt
2.2-HOAt
2.3-OxymaPure
2.4-Oxyma-B
3- H-Gly-Ser-Phe-NH2 racemization Experiments
3.1-HOBt
3.2-HOAt
3.3-OxymaPure
3.4-Oxyma-B
4- H-Gly-Cys-Phe-NH2 racemization experiments
4.1-HOBt
4.2-HOAt
4.3-OxymaPure
4.4-Oxyma-B
5- H-Gly-Cys(Acm)-Phe-NH2 racemization experiments
5.1-HOBt
5.2-HOAt
5.3-OxymaPure
5.4-Oxyma-B
6- H-Gly-His-Phe-NH2 racemization experiments
6.1-HOBt
6.2-HOAt
6.3-OxymaPure
6.4-Oxyma-B
7- Peptide synthesis experiments (Synthesis of H-Tyr-Aib-Aib-Phe-Leu-NH2)
7.1- HOBt
7.2- HOAt
7.3- OxymaPure
7.4-Oxyma-B (without preactivation)
7.5-Oxyma-B (3 min preactivation)
7.6-Oxyma-B (3 min preactivation with 0.1 eq. DIEA)
7.7-Oxyma-B (7 min preactivation)