Solid-phase synthesis of callipeltin D. Stereochemical confirmation of the unnatural amino acid AGDHE

被引:13
作者
Cranfill, DC
Morales-Ramos, AI
Lipton, MA
机构
[1] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA
[2] Purdue Univ, Ctr Canc, W Lafayette, IN 47907 USA
关键词
D O I
10.1021/ol052438f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The lipopeptide callipeltin D (1) was synthesized using an Fmoc-based solid-phase strategy in seven steps and 35% overall yield. The H-1 NMR of synthetic 1 correlated closely with that of the natural product, confirming the configurational assignment of the novel amino acid constituent (2R,3R,4S)-4-amino-7-guanidino-2,3-dihydroxyheptanoic acid.
引用
收藏
页码:5881 / 5883
页数:3
相关论文
共 15 条
[1]   Synthesis and analysis of the sterically constrained L-glutamine analogues (3S,4R)-3,4-dimethyl-L-glutamine and (3S,4R)-3,4-dimethyl-L-pyroglutamic acid [J].
Acevedo, CM ;
Kogut, EF ;
Lipton, MA .
TETRAHEDRON, 2001, 57 (30) :6353-6359
[2]  
BARLOS K, 1991, INT J PEPT PROT RES, V37, P513
[3]  
BARLOS K, 1991, INT J PEPT PROT RES, V38, P555
[4]   Synthesis of N-Fmoc-(2S,3S,4R)-3,4-dimethylglutamine:: An application of lanthanide-catalyzed transamidation [J].
Çalimsiz, S ;
Lipton, MA .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6218-6221
[5]   Chiron approach to callipeltin A:: first synthesis of fully protected (2R,3R,4S)-4,7-diamino-2,3-dihydroxy heptanoic acid [J].
Chandrasekhar, S ;
Ramachandar, T ;
Rao, BV .
TETRAHEDRON-ASYMMETRY, 2001, 12 (16) :2315-2321
[6]  
DAuria MV, 1996, TETRAHEDRON, V52, P9589
[7]   Progress towards the total synthesis of callipeltin A.: Asymmetric synthesis of (2R,3R,4S)-3-hydroxy-2,4,6-trimethylheptanoic acid [J].
Guerlavais, V ;
Carroll, PJ ;
Joullié, MM .
TETRAHEDRON-ASYMMETRY, 2002, 13 (07) :675-680
[8]   An efficient method for activation and recycling of trityl resins [J].
Harre, M ;
Nickisch, K ;
Tilstam, U .
REACTIVE & FUNCTIONAL POLYMERS, 1999, 41 (1-3) :111-114
[9]   Progress toward the total synthesis of callipeltin A (I):: Asymmetric synthesis of (3S,4R)-3,4-dimethylglutamine [J].
Liang, B ;
Carroll, PJ ;
Joullié, MM .
ORGANIC LETTERS, 2000, 2 (26) :4157-4160
[10]   Stereoselective synthesis of (3S,4R)-3,4-dimethyl-(S)-glutamine and the absolute stereochemistry of the natural product from papuamides and callipeltin [J].
Okamoto, N ;
Hara, O ;
Makino, K ;
Hamada, Y .
TETRAHEDRON-ASYMMETRY, 2001, 12 (09) :1353-1358