TY - JOUR
T1 - Synthetic approaches to peptide analogues containing 4, 4‐difluoro‐L‐proline and 4‐keto‐L‐proline
AU - SUFRIN, JANICE R.
AU - BALASUBRAMANIAN, TRICHEY M.
AU - VORA, CHANDRANAN M.
AU - MARSHALL, GARLAND R.
PY - 1982/11
Y1 - 1982/11
N2 - An improved synthesis of 4, 4‐difluoro‐L‐proline is described. A key step in this synthesis involves the fluorination of Z‐4‐keto‐L‐proline benzyl ester, using diethylaminosulfur trifluoride (DAST), to give the corresponding Z‐4, 4‐difluoro‐L‐proline benzyl ester. Preparation of dipeptide derivatives containing 4, 4‐difluoro‐L‐proline has been accomplished by initial synthesis of the corresponding 4‐keto‐L‐proline dipeptide derivatives, which were then fluorinated with DAST. A one‐step synthesis of Boc‐4‐keto‐L‐proline from Boc‐4‐hydroxy‐L‐proline by chromium trioxide oxidation is reported. These synthetic procedures should facilitate the preparation of a variety of peptide analogues containing 4, 4‐difluoro‐L‐proline and 4‐keto‐L‐proline.
AB - An improved synthesis of 4, 4‐difluoro‐L‐proline is described. A key step in this synthesis involves the fluorination of Z‐4‐keto‐L‐proline benzyl ester, using diethylaminosulfur trifluoride (DAST), to give the corresponding Z‐4, 4‐difluoro‐L‐proline benzyl ester. Preparation of dipeptide derivatives containing 4, 4‐difluoro‐L‐proline has been accomplished by initial synthesis of the corresponding 4‐keto‐L‐proline dipeptide derivatives, which were then fluorinated with DAST. A one‐step synthesis of Boc‐4‐keto‐L‐proline from Boc‐4‐hydroxy‐L‐proline by chromium trioxide oxidation is reported. These synthetic procedures should facilitate the preparation of a variety of peptide analogues containing 4, 4‐difluoro‐L‐proline and 4‐keto‐L‐proline.
KW - 4
KW - 4‐difluoro‐L‐proline
KW - Boc‐4‐keto‐L‐proline
KW - diethylaminosulfur trifluoride (DAST)
KW - peptide synthesis
KW - proline analogues
UR - http://www.scopus.com/inward/record.url?scp=0020212110&partnerID=8YFLogxK
U2 - 10.1111/j.1399-3011.1982.tb03065.x
DO - 10.1111/j.1399-3011.1982.tb03065.x
M3 - Article
C2 - 7174207
AN - SCOPUS:0020212110
VL - 20
SP - 438
EP - 442
JO - International Journal of Peptide and Protein Research
JF - International Journal of Peptide and Protein Research
SN - 0367-8377
IS - 5
ER -